trans-2-Carbomethoxycyclopentane-1-carboxylic acid

Base Information

• Chemical Name: trans-2-Carbomethoxycyclopentane-1-carboxylic acid
• CAS No.: 111138-44-4
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.181
• DSSTox Substance ID: DTXSID40445638
• Wikidata: Q82264133
• Mol file: 111138-44-4.mol

Synonyms:111138-44-4;trans-2-Carbomethoxycyclopentane-1-carboxylic acid;trans-2-(methoxycarbonyl)cyclopentanecarboxylic acid;(1R,2R)-2-(Methoxycarbonyl)cyclopentanecarboxylic acid;(1R,2R)-2-methoxycarbonylcyclopentane-1-carboxylic acid;MFCD01311174;111138-68-2;(1R,2R)-2-(Methoxycarbonyl)cyclopentane-1-carboxylic acid;SCHEMBL596153;DTXSID40445638;KYGFHAUBFNTXFK-PHDIDXHHSA-N;CS-0197688;F31418;F50022;EN300-20812569;(1R,2R)-2-(Methoxycarbonyl)cyclopentanecarboxylicacid;rac-(1R,2R)-2-(methoxycarbonyl)cyclopentane-1-carboxylic acid;rac-trans-cyclopentane-1,2-dicarboxylic acid monomethyl ester

Chemical Property of trans-2-Carbomethoxycyclopentane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 286.423°C at 760 mmHg
• PKA: 4.37±0.40(Predicted)
• Flash Point: 114.63°C
• PSA: 63.60000
• Density: 1.242g/cm³
• LogP: 0.66030
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 199

Purity/Quality:

98%min ^*data from raw suppliers

trans-2-Carbomethoxycyclopentane-1-carboxylicacid,97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCC1C(=O)O
• Isomeric SMILES: COC(=O)[C@@H]1CCC[C@H]1C(=O)O

Technology Process of trans-2-Carbomethoxycyclopentane-1-carboxylic acid

There total 5 articles about trans-2-Carbomethoxycyclopentane-1-carboxylic 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: 75.0%

1-methyl hydrogen (1S*,2R*)-1,2-cyclopentanedicarboxylate → (1,2-trans)-2-(methoxycarbonyl)cyclopentanecarboxylic acid (88315-64-4,88335-90-4,92541-43-0,98168-34-4,111138-44-4,111138-48-8,111138-68-2,124916-60-5)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃; for 4h; Inert atmosphere;

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → (1,2-trans)-2-(methoxycarbonyl)cyclopentanecarboxylic acid (88315-64-4,88335-90-4,92541-43-0,98168-34-4,111138-44-4,111138-48-8,111138-68-2,124916-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bromine / chloroform / 0 - 20 °C

1.2: 6 h / 0 °C

1.3: pH 5

2.1: acetic anhydride / 20 h / Reflux

3.1: 24 h / 60 °C / Inert atmosphere

4.1: lithium diisopropyl amide / 4 h / -78 °C / Inert atmosphere

With bromine; acetic anhydride; lithium diisopropyl amide; In chloroform;

Reference yield:

cis-1,2-cyclopentanedicarboxylic acid (1461-96-7) → (1,2-trans)-2-(methoxycarbonyl)cyclopentanecarboxylic acid (88315-64-4,88335-90-4,92541-43-0,98168-34-4,111138-44-4,111138-48-8,111138-68-2,124916-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic anhydride / 20 h / Reflux

2: 24 h / 60 °C / Inert atmosphere

3: lithium diisopropyl amide / 4 h / -78 °C / Inert atmosphere

With acetic anhydride; lithium diisopropyl amide;

upstream raw materials:

methanol

trans-1,2-cyclopentanedicarboxylic acid

ethyl 2-oxocyclohexane carboxylate

cis-1,2-cyclopentanedicarboxylic acid

Downstream raw materials:

(1,2-trans)-N-benzyl-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentanecarboxamide

Refernces