Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate

Base Information

• Chemical Name: Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate
• CAS No.: 87682-85-7
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• DSSTox Substance ID: DTXSID70576085
• Mol file: 87682-85-7.mol

Synonyms:87682-85-7;Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate;Methyl 2-oxo-5-phenylcyclopentanecarboxylate;DTXSID70576085

Chemical Property of Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.094294304
• Heavy Atom Count: 16
• Complexity: 279

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(CCC1=O)C2=CC=CC=C2

Technology Process of Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate

There total 5 articles about Methyl 2-oxo-5-phenylcyclopentane-1-carboxylate 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: 95.0%

methanol (67-56-1) + (+)-neomenthyl 2-oxo-5-phenylcyclopentanecarboxylate → 2-carbomethoxy-3-phenylcyclopentanone (87682-85-7)

Guidance literature:

at 100 ℃; for 18h;

DOI:10.1080/00397919408010251

Reference yield: 66.0%

(E)-dimethyl hex-2-enedioate (70353-99-0) + lithium diphenylcuprate (7237-89-0) → 2-carbomethoxy-3-phenylcyclopentanone (87682-85-7)

Guidance literature:

In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jo00174a043

Reference yield:

methyl 3-oxo-6-phenylhexanoate (79144-70-0) → 2-carbomethoxy-3-phenylcyclopentanone (87682-85-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / toluene / 6 h / Heating

2: 92 percent / methanesulfonyl azide, Et₃N / acetonitrile / 6 h / Ambient temperature

3: 83 percent / Rh₂(R-PTPA)4 / CH₂Cl₂ / 0.5 h / 0 °C

4: 95 percent / 18 h / 100 °C

With Rh₂(R)-(PTPA)4; triethylamine; Methanesulfonyl azide; In dichloromethane; toluene; acetonitrile;

DOI:10.1080/00397919408010251

upstream raw materials:

(E)-dimethyl hex-2-enedioate

lithium diphenylcuprate

methanol

methyl 3-oxo-6-phenylhexanoate

Downstream raw materials:

(R)-3-phenylcyclopentanone

(S)-3-phenylcyclopentanone