2,2-dimethyl-3-phenylcyclopentanone

Base Information

• Chemical Name: 2,2-dimethyl-3-phenylcyclopentanone
• CAS No.: 106988-05-0
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.269
• Mol file: 106988-05-0.mol

Synonyms:2,2-dimethyl-3-phenylcyclopentanone

Chemical Property of 2,2-dimethyl-3-phenylcyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethyl-3-phenylcyclopentanone

There total 5 articles about 2,2-dimethyl-3-phenylcyclopentanone 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: 87.0%

[(E)-3-(2-methylallyloxy)prop-1-enyl]benzene → 2,2-dimethyl-3-phenylcyclopentanone (106988-05-0)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In 1,2-dichloro-ethane; at 80 ℃; for 72h; Concentration; Reagent/catalyst; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol400574s

Reference yield: 5.0%

[(E)-3-(2-methylallyloxy)prop-1-enyl]benzene → (E)-2,2-dimethyl-3-phenylpent-3-enal + 2,2-dimethyl-3-phenylcyclopentanone (106988-05-0)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,4-di(diphenylphosphino)-butane; In 1,2-dichloro-ethane; at 80 ℃; for 16h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/ol400574s

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → 2,2-dimethyl-3-phenylcyclopentanone (106988-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / paraffin oil; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate / 1,2-dichloro-ethane / 72 h / 80 °C / Inert atmosphere; Schlenk technique

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; sodium hydride; In tetrahydrofuran; 1,2-dichloro-ethane; paraffin oil;

DOI:10.1021/ol400574s

upstream raw materials:

2-phenylcyclobutanone

1-chloro-2-<(1-methylethyl)sulfinyl>benzene

(2E)-3-phenyl-2-propen-1-ol

Refernces

• 1、 Gadwood, Robert C.,Mallick, Ishwar M.,DeWinter, Amy J.. "Ring Expansion of Cyclobutanones to Cyclopentanones via α-Lithioalkyl Aryl Sulfoxides and Selenoxides". . p. 774 - 782. Retrieved 2007/10/02.