5709-98-8

Basic information

• Product Name: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID
• Synonyms: (R)-Cyclohex-3-enecarboxylic acid;(R)-(+)-1,2,3,6-Tetrahydrobenzoic acid;(1R)-cyclohex-3-ene-1-carboxylic acid;(R)-cyclohex-3-ene-1-carboxylicacid;(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID;(1R)-3-Cyclohexene-1-carboxylic acid;(R)-3-Cyclohexene-1-carboxylic acid;(R)-3-Cyclohexene-1β-carboxylic acid
• CAS NO: 5709-98-8
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• Product Categories: Chiral Reagents;Chiral Compound
• Mol File: 5709-98-8.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 241.7 °C at 760 mmHg
• Flash Point: 109.9 °C
• Appearance: /
• Density: 1.126 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Methanol
• PKA: 4.67±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(5709-98-8)
• EPA Substance Registry System: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(5709-98-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• Hazardous Substances Data: 5709-98-8(Hazardous Substances Data)

Usage

Description

(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID is an organic compound with the chemical formula C7H10O2. It is a chiral molecule, which means it has a non-superimposable mirror image, and in this case, it is the (R)-enantiomer. (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID is characterized by a cyclohexene ring with a carboxylic acid functional group, making it a cyclohexene carboxylic acid derivative. It is a colorless oil, indicating its low molecular weight and relatively low polarity.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its key applications is in the production of Leustroducsin B (LSN-B), a novel colony-stimulating factor (CSF) inducer. LSN-B is isolated from Streptomyces platensis and has potential applications in the treatment of various diseases and conditions related to the immune system.
As an intermediate in the synthesis of Leustroducsin B, (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID plays a crucial role in the development of new drugs and therapies. Its unique chemical structure allows for further functionalization and modification, enabling the creation of more complex and effective pharmaceutical compounds.

Upstream product

• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 943144-69-2 C₁₇H₁₉NO₃ 
• 136030-00-7 (1R,2S)-1-Amino-2-indanol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 19914-76-2 (1S-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 
• 1352834-06-0 cyclohex-3-ene-1-carboxylic acid (S)-1-phenylethanamine salt 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 
• 119944-89-7 (2S)-N-(acryloyl)bornane-10,2-sultam 
• 106-99-0 buta-1,3-diene 
• 143347-67-5 (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester 

Downstream Products

• 54911-89-6 (1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate 
• 127943-95-7 methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate 
• 1026073-45-9 methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate 
• 1339943-40-6 C₅₆H₇₆O₁₈Si 
• 1339943-42-8 C₅₀H₆₂O₁₈ 
• 1350636-90-6 N-(cyclohex-3-en-1(R)-yl)-2,2,2-trifluoro-acetamide 
• 1350753-51-3 ethyl cyclohex-3-enyl-1(R)-carbamate 
• 1350636-87-1 (R)-(3-cyclohexenyl)carbamic acid tert-butyl ester 
• 1350636-89-3 {(1R,2R,4R)-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclohexyl}phenyl thioformate 
• 1350734-45-0 {(1S,2S,5S)-5-[(tert-butoxycarbonyl)-amino]-2-hydroxy-cyclohexyl} benzenecarbothioate 
• 1350767-92-8 3-cyclohexene-1(R)-amine hydrochloride 
• 1350636-92-8 {(1R,2R,4R)-4-[(2,2,2-trifluoro-acetyl)-amino]-2-hydroxy-cyclohexyl} benzene-carbothioate 
• 1350753-45-5 2-(cyclohex-3-en-1(R)-yl)-isoindole-1,3-dione 
• 1350753-46-6 tert-butyl [(1R,3R,4R)-3-hydroxy-4-tritylsulfanyl-cyclohexyl]-carbamate 

Relevant articles and documents

Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining

A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic methyl 3-cyclohexene-1-carboxylate (rac-CHCM) with a nearly symmetric structure for the synthesis of (S)-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4.0 M (560 g·L-1) rac-CHCM was accomplished, yielding (S)-CHCM with a >99% ee, a substrate to catalyst ratio of 1400 g·g-1, and a space-time yield of 538 g·L-1·d-1.

Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.

An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors

An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the tit