21531-46-4

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(S)-3-oxo-1-cylcohexanecarboxylic acid is used as a key intermediate in the production of pharmaceuticals for its role in the synthesis of antiviral and antibacterial drugs. Its unique structure allows for the development of effective medications targeting a range of viral and bacterial infections.
Used in Agrochemical Industry:
In the agrochemical industry, (+)-(S)-3-oxo-1-cylcohexanecarboxylic acid is utilized in the production of compounds that inhibit the growth of certain pests and pathogens in crops. This application helps to improve crop yields and protect plants from damage caused by various agricultural threats.

Upstream product

• 122743-44-6 (1S,3S)-3-hydroxycyclohexane-1-carboxylic acid 
• 1236384-30-7 (S)-methyl 3-oxocyclohexanecarboxylates 
• 122689-79-6 isopropyl 3-oxocyclohex-1-ene-1-carboxylate 
• 99438-50-3 (1S,3S)-3-hydroxycyclohexane-1-carboxylic acid isopropyl ester 
• 99407-62-2 (+/-)-isopropyl 3-oxocyclohexanecarboxylate 
• 504-02-9 1,3-cylohexanedione 
• 24079-79-6 cyclohexen-3-one-1-carboxylic acid 
• 77708-66-8 3-oxocyclohex-1-en-1-yl 4-methylbenzenesulfonate 
• 90865-32-0 (S)-3-oxo-cyclohexanecarbonitrile 
• 124267-26-1 3-ethynyl-2-cyclohexen-1-one 
• 17983-30-1 (RS)-3-oxocyclohexanecarbonitrile 
• 54396-74-6 3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 
• 21531-47-5 3-oxo-cyclohexanecarboxylic acid methyl ester 
• 5682-75-7 3-chloro-2-cyclohexenone 

Downstream Products

• 115730-34-2 (1S,3R)-1-Amino-cyclohexane-1,3-dicarboxylic acid 
• 1026023-02-8 methyl (S)-3,3-dimethoxycyclohexanecarboxylate 
• 115730-33-1 (1S,3S)-cis-1-amino-1,3-cyclohexanedicarboxylic acid 

Relevant academic research and scientific papers

PROCESS FOR PREPARING CARBAMOYLOXYMETHYL TRIAZOLE CYCLOHEXYL ACID COMPOUNDS

Improved methods and intermediates thereof for preparing carbamoyloxy methyl triazole cyclohexyl acid compounds are described. These compounds are useful as LPA antagonists. Formula (I).

Identification and Implementation of Biocatalytic Transformations in Route Discovery: Synthesis of Chiral 1,3-Substituted Cyclohexanone Building Blocks

Several biocatalytic approaches for the preparation of optically pure methyl 3-oxocyclohexanecarboxylates (S)-, (R)-1 and 3-oxocyclohexanecarbonitriles (S)-, (R)-2 have been successfully demonstrated. Screening of reaction-focused enzyme collections was used to identify initial hits using three enzymatic strategies. Reaction optimization and scale-up enabled the production of chiral intermediates for route scouting efforts on scales of up to 100 g. The enzymes applied in these processes (lipases, enoate reductases, and nitrilases) have been shown to be robust catalysts for drug manufacturing and represent a green alternative to conventional methods to access these chiral cyclohexanone building blocks.

Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction

A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopentene- and cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 °C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 °C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.

Rhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ-oxo-carboxylic acids by oxidation of the furyl ring with ozone

Rhodium-catalyzed 1,4-addition of lithium 5-methyl-2-furyltriolborate ([ArB(OCH2)3CCH3]Li, Ar=5-methyl-2-furyl) to unsaturated ketones to give β-furyl ketones was followed by ozonolysis of the furyl ring for enantioselecti

Rhodium-catalyzed asymmetric 1,4-addition of 2-alkenyl-1,3,2- benzodioxaboroles to α,β-unsaturated ketones

Reaction of 2-alkenyl-1,3,2-benzodioxaboroles, which are readily accessible by hydroboration of alkynes with catecholborane, with α,β- unsaturated ketones in the presence of rhodium/(S)-binap catalyst and triethylamine in dioxane/H2O (10/1) pro

CHEMOENZYMATIC SYNTHESIS OF CONFORMATIONALLY RIGID GLUTAMIC ACID ANALOGUES

All stereomers of cyclohexane cyclopentane-derived analogues of glutamic acid have been synthesized from the corresponding 3-keto-cycloalkyl carboxylic acid esters by a combination of microbial steps and standard chemical methods.