(R)-Cyclohex-3-enecarboxylic acid

Base Information

• Chemical Name: (R)-Cyclohex-3-enecarboxylic acid
• CAS No.: 5709-98-8
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2916200090
• European Community (EC) Number: 634-674-8
• DSSTox Substance ID: DTXSID60353089
• Nikkaji Number: J36.762A
• Wikidata: Q72459761
• Mol file: 5709-98-8.mol

Synonyms:5709-98-8;(R)-Cyclohex-3-enecarboxylic acid;(R)-3-CYCLOHEXENECARBOXYLIC ACID;(1R)-cyclohex-3-ene-1-carboxylic acid;(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID;(R)-3-Cyclohexene-1-carboxylic acid;3-Cyclohexene-1-carboxylic acid, (1R)-;MFCD08275445;(R)-Cyclohex-3-enecarboxylicacid;SCHEMBL468428;AMY4035;DTXSID60353089;3-cyclohexene-1(R)-carboxylic acid;3-Cyclohexene-1beta-carboxylic acid;AKOS016843451;(1R)-3-Cyclohexene-1-carboxylic Acid;DS-17171;(R)-(+)-3-Cyclohexene-1-carboxylic acid;CS-0021761;EN300-218754;A858255

Chemical Property of (R)-Cyclohex-3-enecarboxylic acid

Chemical Property:

• Boiling Point: 241.7 °C at 760 mmHg
• PKA: 4.67±0.20(Predicted)
• Flash Point: 109.9 °C
• PSA: 37.30000
• Density: 1.126 g/cm³
• LogP: 1.42730
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-CyclohexenecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC=C1)C(=O)O
• Isomeric SMILES: C1C[C@H](CC=C1)C(=O)O
• Uses: An intermediate of Leustroducsin B (LSN-B), a novel colony-stimulating factor (CSF) inducer, which was isolated from Streptomyces platensis. An intermediate of Leustroducsin B (LSN-B)

Technology Process of (R)-Cyclohex-3-enecarboxylic acid

There total 28 articles about (R)-Cyclohex-3-enecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (143347-67-5) → (R)-cyclohex-3-enecarboxylic acid (5709-98-8)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo00045a013

Reference yield: 94.0%

3-Cyclohexene-1-carboxylic acid (S)-pantolactone ester (127604-94-8) → (R)-cyclohex-3-enecarboxylic acid (5709-98-8)

Guidance literature:

3-Cyclohexene-1-carboxylic acid (S)-pantolactone ester; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 26h;

In water; pH=2; Acidic aq. solution;

DOI:10.1016/j.tet.2011.01.064

Reference yield: 89.0%

(R)-1-C-(1-Cyclohexen-5-yl)methanol (5709-99-9) → (R)-cyclohex-3-enecarboxylic acid (5709-98-8)

Guidance literature:

With chromium(VI) oxide; In acetone; for 0.0666667h; Ambient temperature;

DOI:10.1002/hlca.19850680803

upstream raw materials:

1,2,5,6-tetrahydrobenzoic acid

cyclohex-3-enylmethanol

(R)-1-C-(1-Cyclohexen-5-yl)methanol

(+)-N-<(R)-cyclohex-3-enylcarbonyl>bornane-10,2-sultam

Downstream raw materials:

(1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohexanecarboxylic acid methyl ester

(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propenal

methyl (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carboxylate

Refernces

• 1、 Dou, Zhe,Chen, Xuanzao,Niwayama, Satomi,Xu, Guochao,Ni, Ye. "Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining". supporting information. p. 3043 - 3047. Retrieved 2021/05/05.
• 2、 Fujita, Ryunosuke,Hayashi, Wakana,Kubota, Shunichi,Nishi, Tatsuya,Nishiyama, Akira,Ochiai, Hidenori,Sasagawa, Miwa. "Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction". . . Retrieved 2022/02/09.