Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)
• CAS No.: 623935-92-2
• Molecular Formula: C12H20O2
• Molecular Weight: 196.286
• Mol file: 623935-92-2.mol

Synonyms:Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)

Chemical Property of Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)

Chemical Property:

• Boiling Point: 243.2±29.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.958±0.06 g/cm3(Predicted)
• LogP: 2.93200

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI)

There total 5 articles about Cyclopentanecarboxylic acid, 2-methyl-5-(1-methylethylidene)-, ethyl ester, (2R)- (9CI) 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: 90.0%

ethanol (64-17-5) + pulegone (89-82-7,90449-51-7) → ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate (623935-92-2)

Guidance literature:

pulegone; With bromine; sodium hydrogencarbonate; In diethyl ether; at -10 ℃; for 2.16667h; Inert atmosphere;

ethanol; With sodium; In diethyl ether; at 55 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jacs.1c00525

Reference yield: 75.0%

pulegone (89-82-7,90449-51-7) → ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate (623935-92-2)

Guidance literature:

pulegone; With bromine; sodium hydrogencarbonate; In diethyl ether; at 0 ℃; for 4h;

With sodium ethanolate; In diethyl ether; ethanol; at 0 ℃; Reflux;

DOI:10.1021/jo2018558

Reference yield: 66.0%

pulegone (89-82-7,90449-51-7) + sodium ethanolate (141-52-6) → ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate (623935-92-2)

Guidance literature:

pulegone; With bromine; sodium hydrogencarbonate; In diethyl ether; Cooling with ice; Inert atmosphere;

sodium ethanolate; at 20 ℃; Cooling with ice;

With semicarbazide hydrochloride; sodium acetate; In ethanol; water; for 3h; Reflux;

upstream raw materials:

(R)-pulegone dibromide

sodium ethanolate

pulegone

ethanol

Downstream raw materials:

((1S,2S,5R)-2-hydroxy-5-methylcyclopentyl)methyl 4-methylbenzenesulfonate

C₂₁H₂₀N₂O₈

(1S,5R)-trans-pulegenic acid

tert-butyl 4-((5R,7S)-5-methyl-7-((4-nitrobenzoyl)oxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate

Refernces

• 1、 -. "Cyclopenta [d] pyrimidine compound, pharmaceutically acceptable salt, solvate or prodrug thereof and application". Paragraph 0219-0224. . Retrieved 2020/07/15.
• 2、 Blake, James F.,Xu, Rui,Bencsik, Josef R.,Xiao, Dengming,Kallan, Nicholas C.,Schlachter, Stephen,Mitchell, Ian S.,Spencer, Keith L.,Banka, Anna L.,Wallace, Eli M.,Gloor, Susan L.,Martinson, Matthew,Woessner, Richard D.,Vigers, Guy P.A.,Brandhuber, Barbara J.,Liang, Jun,Safina, Brian S.,Li, Jun,Zhang, Birong,Chabot, Christine,Do, Steven,Lee, Leslie,Oeh, Jason,Sampath, Deepak,Lee, Brian B.,Lin, Kui,Liederer, Bianca M.,Skelton, Nicholas J.. "Discovery and preclinical pharmacology of a selective ATP-competitive Akt inhibitor (GDC-0068) for the treatment of human tumors". . p. 8110 - 8127. Retrieved 2012/11/13.