2-Phenylcyclobutanone

Base Information

• Chemical Name: 2-Phenylcyclobutanone
• CAS No.: 42436-86-2
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Hs Code.: 2914399090
• DSSTox Substance ID: DTXSID90466792
• Nikkaji Number: J89.462A
• Mol file: 42436-86-2.mol

Synonyms:2-phenylcyclobutanone;2-phenylcyclobutan-1-one;42436-86-2;MFCD19382274;2-phenyl-cyclobutan-1-one;SCHEMBL13210441;DTXSID90466792;AKOS022179919;SB10969;AS-42272;SY029844;CS-0051808;EN300-80618;F8880-8488

Chemical Property of 2-Phenylcyclobutanone

Chemical Property:

• PSA: 17.07000
• LogP: 2.13310
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

98%min ^*data from raw suppliers

2-Phenylcyclobutan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C1C2=CC=CC=C2
• Uses: 2-Phenylcyclobutan-1-one is a useful reagent for the green preparation of γ, δ- and ?-keto esters.

Technology Process of 2-Phenylcyclobutanone

There total 31 articles about 2-Phenylcyclobutanone 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: 94.3%

1-(Hydroxy-phenyl-methyl)-cyclopropanol (246180-23-4) → 2-phenylcyclobutanone (42436-86-2)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/0040-4039(94)02452-H

Reference yield: 89.0%

1-phenylmethylenecyclopropane (7555-67-1) → 2-phenylcyclobutanone (42436-86-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03707

Reference yield: 81.0%

(S)-(+)-1-(1-hydroxycyclopropyl)benzyl alcohol → 2-phenylcyclobutanone (42436-86-2)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1016/0040-4020(95)00226-X

upstream raw materials:

cyclopropyldiphenylsulfonium tetrafluoroborate

benzaldehyde

4,5-epoxy-3-phenyl-hexahydro-pyridazine

diazomethane

Downstream raw materials:

3-phenylcyclopentanone

trans-2-methyl-3-phenylcyclopentan-1-one

cis-2-methyl-3-phenyl-cyclopentanone

2,2-dimethyl-3-phenylcyclopentanone

Refernces

• 1、 Lapez, Mara-A Marta-N,Jamey, Nicolas,Pinet, Alexis,Figadeìre, Bruno,Ferri, Laurent. "Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes". . p. 1626 - 1631. Retrieved 2021/03/08.
• 2、 Bai, Junxue,Li, Miao,Zhou, Cong,Sha, Yu,Cheng, Jiang,Sun, Jianwei,Sun, Song. "Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids". supporting information. p. 9654 - 9658. Retrieved 2021/12/14.