(1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid

Base Information

• Chemical Name: (1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid
• CAS No.: 111955-05-6
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.208
• Hs Code.: 2918990090
• European Community (EC) Number: 855-477-5
• NSC Number: 53943
• DSSTox Substance ID: DTXSID50288053
• Nikkaji Number: J1.071.877E
• Mol file: 111955-05-6.mol

Synonyms:2778-62-3;(1S,2R)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid;88335-92-6;(1s,2r)-2-(methoxycarbonyl)cyclohexanecarboxylic acid;2484-60-8;NSC53943;1,2-Cyclohexanedicarboxylic acid, 1-methyl ester, (1R,2S)-rel-;trans-2-Carbomethoxycyclohexane-1-carboxyic acid;SCHEMBL727158;(1R, 2S)-2-(Methoxycarbonyl)-cyclohexane-carboxylic acid;DTXSID50288053;MFCD26516383;NSC-53943;AKOS034803921;CS-0342671;EN300-395783;A911884;(1 S,2R)-2-(methoxycarbonyl) cyclohexanecarboxylic acid;(1S,2R)-2-(methoxycarbonyl) cyclohexanecarboxylic acid;(1S,2R)-2-(methoxycarbonyl)cyclohexane-1-carboxylicacid;Cyclohexane-1beta,2beta-dicarboxylic acid 1-methyl ester;Z1955918666;(1R, 2S)-1,2Cyclohexanedicarboxylic acid-1-mehtyl ester;rac-(1R,2S)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid;(1S,2R)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid, 98% ee 99%

Chemical Property of (1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000219mmHg at 25°C
• Melting Point: 54 °C
• Boiling Point: 303.1oC at 760 mmHg
• PKA: 4.45±0.44(Predicted)
• Flash Point: 118.3oC
• PSA: 63.60000
• Density: 1.191g/cm3
• LogP: 1.05040
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 186.08920892
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

98% ^*data from raw suppliers

Cis-2-carbomethoxycyclohexane-1-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCCC1C(=O)O
• Isomeric SMILES: COC(=O)[C@@H]1CCCC[C@@H]1C(=O)O

Technology Process of (1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic acid

There total 14 articles about (1s,2r)-2-(Methoxycarbonyl)cyclohexanecarboxylic 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: 100.0%

methanol (67-56-1) + 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → cyclohexane-1,2-dicarboxylic acid monomethyl ester (2484-60-8,2778-62-3,7719-08-6,52782-07-7,88335-91-5,88335-92-6,96894-64-3,111955-05-6)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.2174/1570178614666171130161203

Reference yield: 94.0%

cyclohexane-1,2-dicarboxylic acid monomethyl ester (2484-60-8,2778-62-3,7719-08-6,52782-07-7,88335-91-5,88335-92-6,96894-64-3,111955-05-6) → (1S*,2S*)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid (2484-60-8,2778-62-3,7719-08-6,52782-07-7,88335-91-5,88335-92-6,96894-64-3,111955-05-6)

Guidance literature:

With sodium methylate; In methanol; for 5h; Inert atmosphere; Reflux;

DOI:10.2174/1570178614666171130161203

Reference yield:

methyl cyclohex-1-ene-1-carboxylate (18448-47-0) + carbon dioxide (124-38-9,18923-20-1) → (1S*,2S*)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid (2484-60-8,2778-62-3,7719-08-6,52782-07-7,88335-91-5,88335-92-6,96894-64-3,111955-05-6) + cyclohexane-1,2-dicarboxylic acid monomethyl ester (2484-60-8,2778-62-3,7719-08-6,52782-07-7,88335-91-5,88335-92-6,96894-64-3,111955-05-6)

Guidance literature:

With 1-Ethyl-2,2,6,6-tetramethylpiperidine; [1,1';4',1'']terphenyl; tris-(trimethylsilyl)silane; In N,N-dimethyl-formamide; at 35 ℃; for 0.333333h; Overall yield = 69 percent; UV-irradiation;

DOI:10.1021/acscatal.0c05050

upstream raw materials:

(+/-)-trans-cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester

methyl trans-2-formylcyclohexane-1-carboxylate

methanol

8,8-dichlorobicyclo[4.2.0]octan-7-one

Downstream raw materials:

methyl cyclohex-1-ene-1-carboxylate

methyl cyclohex-2-en-1-carboxylate

(1S*,2S*)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid

methyl trans-2-formylcyclohexane-1-carboxylate

Refernces

• 1、 Uccello Barretta, Gloria,Mandoli, Alessandro,Balzano, Federica,Aiello, Federica,De Nicola, Beatrice,Del Grande, Alessandro. "Monomeric and Dimeric 9-O Anthraquinone and Phenanthryl Derivatives of Cinchona Alkaloids as Chiral Solvating Agents for the NMR Enantiodiscrimination of Chiral Hemiesters". . p. 693 - 699. Retrieved 2015.
• 2、 Laborda, Pedro,Sayago, Francisco J.,Cativiela, Carlos,Gotor, Vicente. "Synthesis of trans-fused octahydroisoindole-1-carboxylic acids". . p. 404 - 411. Retrieved 2018/05/22.