(1R,2S)-1,2-Cyclopentanedicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1R,2S)-1,2-Cyclopentanedicarboxylic acid dimethyl ester
• CAS No.: 4841-91-2
• Molecular Formula: C9H14O4
• Molecular Weight: 186.20500
• Mol file: 4841-91-2.mol

Synonyms:cis-Cyclopentan-dicarbonsaeure-(1.2)-dimethylester;cis-cyclopentane-1,2-dicarboxylic acid dimethyl ester;cis-dimethyl 1,2-cyclopentanedicarboxylate;cis-Cyclopentan-1,2-dicarbonsaeure-dimethylester;dimethyl cis-cyclopentane-1,2-dicarboxylate;(1S,2R)-Cyclopentane-1,2-dicarboxylic acid dimethyl ester;

Chemical Property of (1R,2S)-1,2-Cyclopentanedicarboxylic acid dimethyl ester

Chemical Property:

• PSA: 52.60000
• LogP: 0.74870

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-1,2-Cyclopentanedicarboxylic acid dimethyl ester

There total 17 articles about (1R,2S)-1,2-Cyclopentanedicarboxylic acid dimethyl ester 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: 99.0%

methanol (67-56-1) + cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8) → dimethyl cis-1,2-cyclopentanedicarboxylate (4841-91-2)

Guidance literature:

With quinidine; In toluene; at -55 ℃; for 60h; optical yield given as %ee;

DOI:10.1002/ejoc.200901233

Reference yield: 78.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4) → dimethyl cis-1,2-cyclopentanedicarboxylate (4841-91-2) + trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester (80656-13-9)

Guidance literature:

In diethyl ether;

DOI:10.1002/hlca.19950780512

Reference yield: 10.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + 1,3-dibromo-propane (109-64-8) → dimethyl 2-(prop-2-en-1-yl)butanedioate (1069-40-5) + dimethyl cis-1,2-cyclopentanedicarboxylate (4841-91-2) + dimethyl trans-cyclopentane-1,2-dicarboxylate (80656-12-8)

Guidance literature:

In various solvent(s); Yields of byproduct given; Ambient temperature; electrolsis (Bu₄NBF₄/Bu₄NI, Al anolde, steel cathode);

DOI:10.1021/jo00295a048

upstream raw materials:

diazomethane

cis-1,2-cyclopentanedicarboxylic acid

1-Amino-2,6-dicyan-piperidin

methanol

Downstream raw materials:

trans-1,2-bis(hydroxymethyl)cyclopentane

ditosylate of (+/-)-1,2-bis(hydroxymethyl)cyclopentane

dimethyl trans-cyclopentane-1,2-dicarboxylate

(1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid

Refernces

• 1、 Wang, Yaxin,Hu, Xiafei,Morales-Rivera, Cristian A.,Li, Guo-Xing,Huang, Xin,He, Gang,Liu, Peng,Chen, Gong. "Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds". supporting information. p. 9678 - 9684. Retrieved 2018/07/21.
• 2、 Yokota, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka. "Oxidative carbomethoxylation of alkenes using a Pd(II)/molybdovanadophosphate (NPMoV) system under carbon monoxide and air". . p. 5005 - 5008. Retrieved 2007/10/03.