Ethanone, 1-[1-(2-propenyl)cyclopentyl]- (9CI)

Base Information

• Chemical Name: Ethanone, 1-[1-(2-propenyl)cyclopentyl]- (9CI)
• CAS No.: 152090-71-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Mol file: 152090-71-6.mol

Synonyms:Ethanone,1-[1-(2-propenyl)cyclopentyl]- (9CI)

Chemical Property of Ethanone, 1-[1-(2-propenyl)cyclopentyl]- (9CI)

Chemical Property:

• PSA: 17.07000
• LogP: 2.71190

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethanone, 1-[1-(2-propenyl)cyclopentyl]- (9CI)

There total 4 articles about Ethanone, 1-[1-(2-propenyl)cyclopentyl]- (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: 78.0%

chloro-trimethyl-silane (75-77-4) + 1-(3-propenyl)cyclopentanecarboxylic acid (411238-08-9) + methyllithium (917-54-4) → 1-Acetyl-1-(2-propenyl)cyclopentane (152090-71-6)

Guidance literature:

1-(3-propenyl)cyclopentanecarboxylic acid; methyllithium; In tetrahydrofuran; diethyl ether; at 0 ℃; for 2h;

chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h;

DOI:10.1002/chem.201503653

Reference yield: 53.0%

1-(3-propenyl)cyclopentanecarboxylic acid (411238-08-9) + methyllithium (917-54-4) → 1-Acetyl-1-(2-propenyl)cyclopentane (152090-71-6)

Guidance literature:

In diethyl ether; at -78 ℃; for 5h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.7b01975

Reference yield:

methyl 1-allylcyclopentane-1-carboxylate (153579-96-5) → 1-Acetyl-1-(2-propenyl)cyclopentane (152090-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / methanol; water / Inert atmosphere; Reflux

2: diethyl ether / 5 h / -78 °C / Inert atmosphere; Reflux

With potassium hydroxide; In methanol; diethyl ether; water;

DOI:10.1021/acs.orglett.7b01975

upstream raw materials:

chloro-trimethyl-silane

1-(3-propenyl)cyclopentanecarboxylic acid

methyllithium

cyclopentanecarboxylic acid

Downstream raw materials:

1-Acetyl-1-(2-oxoethyl)cyclopentane

Refernces

• 1、 Percy, Jonathan M.,McCarter, Adam W.,Sewell, Alan L.,Sloan, Nikki,Kennedy, Alan R.,Hirst, David J.. "Developing the Saegusa-Ito Cyclisation for the Synthesis of Difluorinated Cyclohexenones". supporting information. p. 19119 - 19127. Retrieved 2016/01/26.