5708-19-0

Basic information

• Product Name: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID
• Synonyms: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID;(1S)-cyclohex-3-ene-1-carboxylic acid;(S)-Cyclohex-3-enecarboxylic acid;(S)-3-Cyclohexene-1-carboxylic Acid;(S)-(?)-1,2,3,6-Tetrahydrobenzoic acid;(1S)-3-Cyclohexene-1-carboxylic acid;(S)-(-)-3-Cyclohexene-1-carboxylic Acid
• CAS NO: 5708-19-0
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 1592732-453-0
• Product Categories: Edoxaban
• Mol File: 5708-19-0.mol
• Article Data: 28

Chemical Properties

• Melting Point: 19°C(lit.)
• Boiling Point: 118°C/6mmHg(lit.)
• Flash Point: 109.903 °C
• Appearance: /
• Density: 1.126 g/cm³
• Refractive Index: 1.4780 to 1.4820
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.67±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)
• EPA Substance Registry System: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGIII
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5708-19-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5708-19-0 differently. You can refer to the following data:
1. (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.
2. (S)-3-Cyclohexene-1-carboxylic Acid has been used as a reactant for the preparation of N-[(1R,2S,5S)-2-{[(5-chloroindol-2-yl)carbonyl]amino}-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride, a potent and orally active direct inhibitor of factor Xa.

Synthesis

54.94 g of cyclohex-3-ene-1(S)-carboxylic acid (R)-(+)-methylbenzylamine salt and 18.2 volumes of H2O were charged to a flask at 20-25°C and stirred. To the mixture obtained further 6.7 volumes of H2O and 10 volumes of EtOAc were added. The mixture obtained was stirred for 15 min, the phases were separated and the organic layer was discarded. The aqueous layer was treated with 10 volumes of MTBE and 2.5 equivalents of 6M HCI were added slowly. The mixture obtained was stirred and two layers were formed, separated and the aqueous layer was extracted with MTBE. The organic layers obtained were combined and washed with aqueous, 30percent NaCl solution. The organic phase obtained was dried over Na2S04, filtered, and from the filtrate obtained solvent was removed in vacuo. Cyclohex-3-ene-1(S)-carboxylic acid in the form of a clear oil was obtained. Yield: 26.13 g (93.3percent of theory).

Upstream product

• 131556-48-4 (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1228540-49-5 Ethyl (R)-3-cyclohexene-1-carboxylate 
• 15111-56-5 ethyl-3-cyclohexene-1-carboxylate 
• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 116733-45-0 3-<(1R)-3-Cyclohexen-1-ylcarbonyl>-1,3-oxazolidin-2-one 
• 943144-69-2 C₁₇H₁₉NO₃ 
• 102096-60-6 (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate 
• 106-99-0 buta-1,3-diene 
• 119944-89-7 (2S)-N-(acryloyl)bornane-10,2-sultam 

Downstream Products

• 6493-77-2 (S)-(-)-methyl 3-cyclohexene-1-carboxylate 
• 480452-36-6 carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester 
• 480449-70-5 edoxaban 
• 929693-31-2 {(1R,2R,4S)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexyl}methanesulfonate 
• 929693-30-1 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexanecarboxamide 
• 40967-78-0 3-aminoadipic acid 
• 912273-65-5 N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2R,4S)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid 
• 123536-65-2 (5S)-5-hydroxymethyl-2-cyclohexen-1-one 
• 179091-38-4 (1S,4S)-4-Benzyloxymethyl-cyclohex-2-enol 
• 184025-97-6 C₂₀H₂₄O₃Se 
• 184025-27-2 ((1S,6S)-6-Benzyloxymethyl-cyclohex-2-enyl)-acetic acid ethyl ester 
• 179091-39-5 ((1S,2S)-2-But-3-ynyl-cyclohex-3-enylmethoxymethyl)-benzene 
• 178945-62-5 (3aS,4S,7aS)-4-Benzyloxymethyl-1-methylene-octahydro-indene 
• 184025-35-2 [(1S,2S)-2-(2-Bromo-ethyl)-cyclohex-3-enylmethoxymethyl]-benzene 

Relevant articles and documents

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.

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.

Preparation method of edoxaban

The invention relates to a new preparation route and a new method for a p-toluenesulfonic acid edoxaban hydrate and intermediates thereof. The new method comprises the steps that a high-reactivity compound 109A4x is prepared; a compound 109C6x is prepared by using a new synthesizing method; new compounds 109E8-01, 109E9x and 109T7-01 are prepared; the p-toluenesulfonic acid edoxaban hydrate is prepared by using the intermediates. By using the new method and the new route, the reaction step of copious cooling is omitted, and dangerous elemental sulfur, high-risk n-butyllithium and high-risk azides are prevented from being used. In a word, by means of the method, the p-toluenesulfonic acid edoxaban hydrate and the key intermediates thereof are more easily and safely prepared at a lower coston an industrialization scale.