Category: 610-09-3

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereochemistry of catalytic hydrogenation. V. The assignment of cis and trans configurations》. Authors are Linstead, R. P.; Davis, Selby B.; Whetstone, Richard R..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Synthetic Route of C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cis-Hexahydrodiphenic acid (m. 240-1°) (I) with concentrated and fuming HNO3 gives only NO2 products and KMnO4 yields no useful products. I. (1g.) in 20 cc. warm AcOH, treated with O3 for 4 hrs. and then overnight with 50 cc. 3% H2O2 and the material separated by fractional acidification, gives about 0.5 g. unchanged I and 128 mg. (crude) cis-hexahydrophthalic acid (identified as the cis-dianilide, m. 238° and the phenylimide). This establishes the structure of I, of the acid m. 289° as cis-syn-cis-perhydrodiphenic acid and of the acid m. 223° as the trans-syn-trans isomer. trans-Δ10-9-Ketododecahydrophenanthrene (Rapson and Robinson, C. A. 29, 7996.1) with O3 in AcOH gives 2.45 g. of trans-2-keto-1, 1′-bicyclohexyl-2′-carboxylic acid (II), a pale yellow oil, isolated as the oxime (3.07g.), m. 162-3°. On acetylation and subsequent pyrolysis II is converted into an unsaturated lactone (not obtained pure) which is oxidized by KMnO4 to a poor yield of trans-hexahydrophthalic acid, m. 227-9° (after repeated crystallization from H2O; 215-20° given in the literature). This series of reactions is not as unequivocal as the oxidation of I. cis-9-Keto-as-octahydrophenanthrene (III) (cf. part VI) (0.4 g.), heated on the steam bath for 15 min. with 5 cc. concentrated HNO3 and 3 cc. fuming HNO3, gives 20 mg. cis-nitrohexahydrodiphenic acid (IV), m. 217-19°, and 0.1 g. of a tri-NO2 derivative of III, m. 151-2°. Heating 500 mg. of III with 1 cc. concentrated HNO3 and 1 cc. fuming HNO3 gives a di-NO2 derivative of III, m. 152°; this gives the tri-NO2 derivative with HNO3 on the steam bath. trans-III (350 mg.) with HNO3 gives about equal amounts (100 mg.) of trans-IV and the tri-NO2 derivative, needles from AcOH, m. 182-4°, or plates from hexane, m. 182.5-3.5°. The stereochem. implications of these results are discussed and it is shown that they are in agreement with other, less exact, evidence.

As far as I know, this compound(610-09-3)Synthetic Route of C8H12O4 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of aromatic compounds with the aid of platinum. III. Hydrogenation with platinum containing oxygen》. Authors are Willstatter, Richard; Jaquet, Daniel.The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).SDS of cas: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. C. A. 7, 1508. Certain reductions, like that of phthalic anhydride (a), which cannot be effected catalytically with Pt free from O, can be initiated by loading the Pt with O and brought to completion by again treating the Pt with O as the catalyst gradually loses its O by the formation of H2O. Oxygen-free Pt and that containing O behave like 2 different contact substances in reduction processes. Thus, 20.3 g. (a) in 75 cc. glacial AcOH with 5 g. Pt absorbed only 400 cc. H; if, however, the H gasometer was shut off and the reaction bulb evacuated, then allowed to fill with air, shaken 1 min. (whereupon O was rapidly absorbed -about 5 cc. per g. Pt) and the air was driven out with H, about 500 cc. of H was again absorbed after each such activation until the 20th and 21st times, when the absorption of H was 1230 and 5600 cc., rasp. The total absorption was 17040 cc. (20°, 760 mm.) or, deducting about 1150 cc. used up by the O introduced in the activations, 15890 cc. or 4.8 mols. Of the 2 rings in (a) the 5-membered one is reduced before the C6H6 ring; the first product is phthalide (b) which is partially reduced to hexahydrophthalide (c) and partially to o-MeC6H4CO2H (d) which is then reduced to the hexahydrotoluic acid (e). If the process is interrupted when only a little H has been absorbed there is obtained, besides some C6H6(CO2H)2, a mixture of (b) and (c), and while (b) is easily reduced further to (d), (c) cannot be reduced to (e). If in the process of isolation alkali is employed the (c) is in part obtained as methylolhexahydrobenzoic acid. Among the reduction products is also cis-hexahydrophthalic acid (f). In the reduction described above were obtained 7 g. (c) (partially hydrolyzed), 7 g. (e) and 4 g. (f). In a similar reduction of (b) 3.4 mols. H were absorbed and there were obtained about equal parts of (e) and (c). Phthalimide behaves quite differently from (a) on reduction, the aromatic nucleus and not the CO groups taking up the O. The activation of the Pt with O is not necessary but the reduction is successful only with the best Pt sponge preparations; many which were active towards C6H6 were inactive towards the imide. Nor can MeOH, EtOH or cyclohexane be used as a solvent; in glacial AcOH the reduction proceeds smoothly. cis-Hexahydrophthalimide seps. from H2O, alc. and AcOH in monoclinic prisms, m. 132°. Naphthalic acid purified by crystallization from alc. cannot be reduced because it always contains some anhydride (g) but the acid freshly precipitated from alk. solution can be reduced; contrary to C10H8, it takes up only 4 atoms of H; the tetrahydronaphthalic acid (h) seps. in cube-like prisms, m. 196° with loss of H2O and conversion into the anhydride, m. 119°. (g), like (a), can be reduced only with Pt activated with O; after about 4 mols. H2 have been absorbed the reaction slows up. As far as the (g) itself is reduced, the anhydride ring is attacked, but as some of the (g) is hydrolyzed by the H2O formed, some (h) is obtained. Among the reduction products are tetrahydro-1-methylnaphthalene-8-carboxylic acid (i), tetra- and decahydronaphthalides and a small amount of decahydroacenaphthene. The 2 naphthalides could not be isolated pure. The (i) seps. from Et2O-petr. ether in needles, m. 150°. o-C6H4(CO2H)2 is easily reduced in AcOH when entirely free from the anhydride, yielding exclusively the cis-hexahydro acid, m. 191-2°. The p-acid in AcOH suspension is reduced much more rapidly on gentle warming, giving about equal parts of the cis- and cis-trans-hexahydro acids, m. 162-3° and about 300°, resp. The m-acid, if pure, is likewise easily reduced in AcOH suspension, forming chiefly the cis- and some cis-trans-hexahydro acid. p-Toluylic acid very quickly gives exclusively or almost exclusively the liquid hexahydro acid whose amide m. 175-6°. Indole in AcOH smoothly absorbs 8 atoms H with formation of perhydroindole, b720 182-3°, b12 65°, a basic oil of medium consistency and unpleasant, penetrating, onion-like odor, d420 0.9947; chloroplatinate, reddish yellow monoclinic tablets from alc., m. 172-3° (not sharply); picrate, fine needles from alc., m. 137-8° (not sharply). If the reduction is interrupted before it is complete (e. g., when 2 atoms of H have been absorbed), the product contains unchanged indole, dihydroindole and perhydroindole, the last being removed by shaking the Et2O solution with 0.1 N HCl until the alk. reaction just disappears, and the first two being separated by fractional precipitation from Et2O with picric acid.

When you point to this article, it is believed that you are also very interested in this compound(610-09-3)SDS of cas: 610-09-3 and due to space limitations, I can only present the most important information.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Safety of cis-Cyclohexane-1,2-dicarboxylic acid. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Probing Single-Chain Magnets in a Family of Linear Chain Compounds Constructed by Magnetically Anisotropic Metal-Ions and Cyclohexane-1,2-Dicarboxylate Analogues. Author is Zheng, Yan-Zhen; Xue, Wei; Tong, Ming-Liang; Chen, Xiao-Ming; Zheng, Shao-Liang.

Five new metal-carboxylate chain-based laminated compounds, namely, ∞2[FeII(e,e-trans-1,2-chdc)] (3) (1,2-chdc = cyclohexane-1,2-dicarboxylate), ∞2[NiII(μ-OH2)(e,a-cis-1,2-chdc)] (4), ∞2[CoII(μ-OH2)(1,2-chedc)] (5) (1,2-chedc = cyclohex-1-ene-1,2-dicarboxylate), ∞2[CoII5(μ3-OH)2(OH2)2(1,2-chedc)4] (6), and ∞2[CoII(4-Me-1,2-chdc)] (7) (4-Me-1,2-chdc = trans-4-methylcyclohexane-1,2-dicarboxylate) were hydrothermally synthesized. In these series of magnetic chain-based compounds, 3 and 7 have the same dimeric paddle-wheel M(II)-carboxylate chain as the previously reported compound, ∞2[CoII(trans-1,2-chdc)] (2). However, compound 3 does not behave as a single-chain magnet (SCM) but simply an alternating ferro-antiferro magnetic chain. Compound 4 has the cis conformation of 1,2-chdc ligand, which leads to a uniform aqua-carboxylate-bridged Ni(II) chain. Such a Ni-O chain exhibits strong antiferromagnetic interactions, leading to a diamagnetic ground state. Compound 5 features a corner-sharing triangular chain, or Δ-chain, which is part of a Kagome lattice. However, 5 does not exhibit a spin-frustrated effect but simply spin competition. Compound 6 has a unique pentanuclear CoII cluster, which is further connected by the syn-anti carboxylate into a chain structure. Compound 6 exhibits antiferromagnetic interactions among the Co(II) ions, and no SCM behavior is observed These results might indicate that the dimeric paddle-wheel Co(II)-carboxylate chain is essential in obtaining SCM behavior in this family of compounds Although 2 and 7 have very similar SCM behavior, a.c. magnetic studies show that 7 has a higher energy barrier than that of 2. Such behavior is probably caused by the larger anisotropic energy barrier in 7.

When you point to this article, it is believed that you are also very interested in this compound(610-09-3)Safety of cis-Cyclohexane-1,2-dicarboxylic acid and due to space limitations, I can only present the most important information.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Category: benzisoxazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Stimulation of pollen tube growth in vitro by dicarboxylic acids. Author is Iwanami, Y..

At 50 ppm, capric acid [334-48-5] and 2-decenoic acid [3913-85-7] almost totally inhibited the germination of Camellia japonica pollen. Moderate inhibition was shown by traumatic acid [6402-36-4], caprylic acid [124-07-2], and IAA [87-51-4]. The above compounds also inhibited pollen tube elongation. At 10 ppm, oxalic acid [144-62-7], succinic acid [110-15-6], suberic acid [505-48-6], adipic acid [124-04-9], sebacic acid [111-20-6], cis-1,2-cyclohexanedicarboxylic acid [610-09-3], and 3,3-diethylglutaric acid [4160-95-6] stimulated pollen tube elongation.

When you point to this article, it is believed that you are also very interested in this compound(610-09-3)Category: benzisoxazole and due to space limitations, I can only present the most important information.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Application of 610-09-3. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about [Ni(cyclam)]2+ and [Ni(R,S-Me6cyclam)]2+ as Linkers or Counterions In Uranyl-Organic Species with cis- and trans-1,2-Cyclohexanedicarboxylate Ligands.

The macrocyclic species [Ni(cyclam)]2+ and [Ni(R,S-Me6cyclam)]2+ were used as addnl. cations in the solvo-hydrothermal synthesis of five uranyl ion complexes with cis- or trans-1,2-cyclohexanedicarboxylic acids (c-1,2-chdcH2 and t-1,2-chdcH2). In the complex [UO2(c-chdc)2Ni(cyclam)(H2O)] (1), dimeric uranyl dicarboxylate subunits are assembled into a two-dimensional (2D) network through axial coordination of NiII to carboxylate groups. Although they involve different isomers, the complexes [(UO2)2(c-chdc)2(c-chdcH)2Ni(cyclam)] (2) and [(UO2)2(t-chdc)2(t-chdcH)2Ni(cyclam)] (3) are very similar, both containing uranyl-based one-dimensional (1D) subunits which are assembled into 2D networks by bridging [Ni(cyclam)]2+ groups. The orientation of the uncoordinated carboxylic group is different in 2 and 3, the layers in 2 being hydrogen bonded to each other through carboxylic acid dimer formation. Using the pure (1R,2R) enantiomer of t-1,2-chdcH2 gives the complex [Ni(cyclam)][(UO2)5(R-t-chdc)3(R-t-chdcH)(O)2(CH3COO)] (4), in which pentanuclear uranyl subunits are assembled into 1D chains by dicarboxylic/-ate ligands in the usual bis(equatorial) chair conformation, another ligand in the divergent bis(axial) conformation uniting these chains into a 2D assembly; the [Ni(cyclam)]2+ ions are simple counterions and are stacked in parallel fashion between the layers. [Ni(R,S-Me6cyclam)][Ni(R,S-Me6cyclam)(H2O)2][(UO2)2(t-chdc)2(O)]2 (5), in which the (1R,2R) enantiomer of t-chdcH2 used has undergone racemization, contains discrete bis(μ3-oxo)-centered tetranuclear uranyl complexes, organized into columns and layers by extensive hydrogen bonding to the counterions. The discoidal shape, available axial coordination sites, and hydrogen bond donor potential of these macrocyclic NiII complexes make them efficient assembling agents in uranyl-organic coordination polymers. As often observed in the presence of d-block metal cations, uranyl luminescence is either completely or partially quenched in complexes 1 and 3, resp.

When you point to this article, it is believed that you are also very interested in this compound(610-09-3)Application of 610-09-3 and due to space limitations, I can only present the most important information.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Related Products of 610-09-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about FT-IR and FT-Raman spectroscopy study of the cyclic anhydride intermediates for the esterification of cellulose. Part 3. Cyclic anhydrides formed by the isomers of cyclohexanedicarboxylic acid. Author is Yang, Charles Q.; Zhang, Guobao.

Multifunctional carboxylic acids were used as crosslinking agents for cotton and wood pulp cellulose. In the authors’ previous research, the authors found that a polycarboxylic acid esterifies cellulose through the formation of a 5-membered cyclic anhydride intermediate by the dehydration of 2 carboxyl groups. The authors studied the formation of those cyclic anhydride intermediates by different isomers of cyclohexanedicarboxylic acid (CHA) so that the authors can elucidate the effects of mol. structure on the formation of the anhydride intermediates. The authors found that both cis- and trans-1,2-CHA form 5-membered anhydride intermediates when temperature reaches their m.p. and that cis-1,2-CHA forms the cyclic anhydride at temperatures lower than does trans-1,2-CHA. 1,3-CHA forms 6-membered cyclic anhydride at temperatures much higher than its m.p. The formation of a 5-membered cyclic anhydride intermediates takes place at temperatures lower than that of a 6-membered anhydride. This is probably the main reason why those polycarboxylic acids with their carboxylic acid groups bonded to the adjacent carbons of the mol. backbones are more effective crosslinking agents for cellulose than those with their carboxylic groups bonded to the alternative carbons. No formation of cyclic anhydride was found for 1,4-CHA. The formation of a 5-membered cyclic anhydride was accelerated by monosodium phosphate, which is used as a catalyst for the esterification of cotton cellulose by polycarboxylic acids.

When you point to this article, it is believed that you are also very interested in this compound(610-09-3)Related Products of 610-09-3 and due to space limitations, I can only present the most important information.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Haddadin, M. J.; Higuchi, T.; Stella, V. published an article about the compound: cis-Cyclohexane-1,2-dicarboxylic acid( cas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O ).Product Details of 610-09-3. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:610-09-3) through the article.

The reversible reactions of several cyclic anhydrides with HOAc to form Ac2O and the corresponding dicarboxylic acid, catalyzed by HClO4 at 25°, were studied. The equilibrium constants calculated from spectral data, were 4.85 × 10-4, 1.08 × 10-1, and 4.6 × 10-1 M for succinic, trans-1,2-cyclohexanedicarboxyllic, and glutaric anhydrides, resp. Maleic, phthalic, and cis-1,2-cyclohexanedicarboxylic anhydrides did not undergo any detectable reaction with HOAc under these conditions, suggesting still higher stability. The reverse rate constants were relatively independent of the structure of the attacking diacid, while the forward rate constants were found to parallel the equilibrium constants The rate-determining step for the forward reaction appears to be the breakdown of the tetrahedral intermediate formed by the attack of HOAc mol. on the protonated cyclic anhydride.

This literature about this compound(610-09-3)Product Details of 610-09-3has given us a lot of inspiration, and I hope that the research on this compound(cis-Cyclohexane-1,2-dicarboxylic acid) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hunsdiecker reaction of silver salts of cis- and trans-1,2-cyclohexanedicarboxylic acid》. Authors are Abell, Paul I..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Reference of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Decarboxylation of the Ag salts of cis- and trans-1,2-cyclohexanedicarboxylic acids (I, Ia) by the action of halogen according to Hunsdiecker, et al. (C.A. 38, 374), gave only trans-1,2-dibromocyclohexane (IIa) through isomerization which appeared to take place at an intermediate stage in the reaction. Com. cis-1,2-cyclohexanedicarboxylic anhydride hydrolyzed in boiling H2O gave I, m. 191-4°, isomerized by heating 8 hrs. at 170-80° with a small amount of dilute HCl in a sealed tube to yield 61.5% Ia, m. 228.5-30.5° (from EtOH). Carefully neutralized solutions of the Na salts of I and Ia treated with an exactly equivalent quantity of aqueous AgNO3 and filtered, the precipitate carefully washed with H2O, alc., and Et2O, dried several days over P2O5 in vacuo, and screened to 100 mesh gave Ag salts (III, IIIa) suitable for reaction with Br. Reaction of III and IIIa with Br was carried out at various temperatures by the inverse addition procedure of Conly (C.A. 48, 2561b) in which the dry III or IIIa was added to Br in CCl4, in an apparatus in which the speed and extent of the reaction were followed by observation of the CO2 evolved. The products of the reaction were tabulated (Ag salt, temperature of reaction, % yield, m.p. IIa, n25D, and structure as shown by infrared spectrum given): III, 0-25°, 43, -4.8°, 1.5503, all trans; III, reflux, 47, -4.7°, 1.5505, all trans; IIIa, 0-25°, 48, -4.5°, 1.5507, all trans; IIIa, reflux, 37, -2.5°, 1.5510, all trans. To establish the stability to isomerization under the above exptl. conditions, known cis-1,2-dibromocyclohexane (II) and IIa were refluxed 12 hrs. with Br and AgBr. II, m. 10.0°, n25D 1.5512, was recovered with a 60% yield of material, m. 6.5°, n25D 1.5511, all cis; and IIa, m. -4.5°, n25D 1.5505, similarly yielded 94% material, m. -4.5°, n25D 1.5505, all trans. Although the data did not distinguish partial isomerization from complete retention of configuration a very large proportion of II survived the reaction. No isomerization of II took place on 12 hrs. refluxing with Br and AgBr in anhydrous CCl4. The mechanistic implications were discussed briefly.

This literature about this compound(610-09-3)Reference of cis-Cyclohexane-1,2-dicarboxylic acidhas given us a lot of inspiration, and I hope that the research on this compound(cis-Cyclohexane-1,2-dicarboxylic acid) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation of aromatic aldehydes with glycine and acetylglycine》. Authors are Dakin, H. D..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Electric Literature of C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

The condensation referred to in the title is complicated by a competing reaction between CH2(NH2)CO2H and BzH, forming a non-acetylated derivative possibly of a type resembling a Schiff base. The 2 reactions are shown thus: (1) H2NCH2CO2H → AcNHCH2CO2H → MeC:N.C(:CHPh).CO.O → MeCONHC(:CHPh)CO2H, (2) HO2CCH2NH2 + BzH → HO2CCH2N:-CHPh (I) or O.CO.CH2.NH.CHPh. I may be called benzylideneglycine and was isolated and analyzed. Because the 2nd condensation product is a non-acetylated compound its formation can be largely suppressed by acetylating the glycine before the reaction. Correspondingly larger yields of the azlactone of α-acetamidocinnamic acid were obtained. Acetylation was most easily effected by warming glycine suspended in 3 parts of glacial AcOH with the theoretical amount of Ac2O until solution was obtained. A variety of aldehydes was used although the product from salicyl aldehyde was the most interesting. AcOC6H4CH:C.N:CMe.O.CO (II) → HOC3H4CH:C(NHAc)CO2H (III) → O.C6H4.CH:C(NHAc).CO (IV). II on treating with alkali and subsequent acidification forms the transient III which quickly passes over to IV. Detailed exptl. data are given.

As far as I know, this compound(610-09-3)Electric Literature of C8H12O4 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Plant Physiology called Structure of some cyclohexyl compounds as related to their ability to stimulate plant growth, Author is Wort, D. James; Patel, Kanti M., which mentions a compound: 610-09-3, SMILESS is O=C([C@H]1[C@@H](C(O)=O)CCCC1)O, Molecular C8H12O4, Electric Literature of C8H12O4.

Of 9 cyclohexyl compounds tested as plant growth regulators on bush bean plants (Phaseolus vulgaris), only cyclohexanecarboxylic (I) [98-89-5] and cyclohexylacetic acid (II) [5292-21-7] significantly increased pod production Among I, II, cyclohexylpropionic [701-97-3], and cyclohexylbutyric acid [4441-63-8], the stimulating effect decreased as the number of CH2 groups in the side chain increased, from 0-3. The effective compounds possessed an H-saturated C6-ring with a single carboxyl group attached directly to the ring or separated by 1 ≤ CH2 group.

As far as I know, this compound(610-09-3)Electric Literature of C8H12O4 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics