3-methyl-5-phenyl-2(5H)-furanone

Base Information

• Chemical Name: 3-methyl-5-phenyl-2(5H)-furanone
• CAS No.: 15121-75-2
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• DSSTox Substance ID: DTXSID00463292
• Nikkaji Number: J1.387.373I
• Mol file: 15121-75-2.mol

Synonyms:3-methyl-5-phenyl-2(5H)-furanone;15121-75-2;3-methyl-5-phenyl-5H-furan-2-one;SCHEMBL7737418;DTXSID00463292;CLEHNEQZYAGENE-UHFFFAOYSA-N

Chemical Property of 3-methyl-5-phenyl-2(5H)-furanone

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(OC1=O)C2=CC=CC=C2

Technology Process of 3-methyl-5-phenyl-2(5H)-furanone

There total 41 articles about 3-methyl-5-phenyl-2(5H)-furanone 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: 100.0%

2-methyl-4-phenyl-2,3-allenoic acid (57496-47-6) → 3-methyl-5-phenylfuran-2-(5H)-one (15121-75-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole); N-ethyl-N,N-diisopropylamine; In acetonitrile; at -15 ℃; for 60h;

DOI:10.1016/S0957-4166(01)00046-5

Reference yield: 98.0%

1-phenylbuta-2,3-dien-1-ol (104516-09-8,124563-14-0,5732-13-8) + carbon monoxide (201230-82-2) → 3-methyl-5-phenylfuran-2-(5H)-one (15121-75-2)

Guidance literature:

With dodecacarbonyl-triangulo-triruthenium; triethylamine; In 1,4-dioxane; at 100 ℃; for 8h; under 7600 Torr;

DOI:10.1021/jo0350615

Reference yield: 94.0%

2α-bromo-2β-methyl-4β-phenyl-γ-butyrolactone (111551-01-0,111551-02-1,119138-44-2,119138-54-4) → 3-methyl-5-phenylfuran-2-(5H)-one (15121-75-2)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

upstream raw materials:

carbon monoxide

(Z)-3-Iodo-1-phenyl-but-2-en-1-ol

exo phenyl-5, exo methyl-2 oxa-4 endo tricyclo<5.2.1.0^2,6>decene-8 one-3

Dihydro-3-(phenylseleno)-3-methyl-5-phenyl-2-furanone

Downstream raw materials:

5-(3-isopropoxyphenyl)-3-methyl-5-phenylfuran-2-one

(S)-(-)-3-methyl-5-phenylfuran-2(5H)-one

(R)-(+)-3-methyl-5-phenylfuran-2(5H)-one

(3R,5S)-3-methyl-5-phenyl-4,5-dihydrofuran-2(3H)-one

Refernces

• 1、 Caine,Frobese. "-". . p. 5167. Retrieved 1978.
• 2、 Shen, Qitao,Yin, Chuanliu,Yu, Chuanming,Zheng, Xiangyun,Zhong, Tianshuo. "Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides". . p. 9699 - 9710. Retrieved 2021/07/26.
• 3、 Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.. "Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts". . p. 2229 - 2238. Retrieved 2019/03/06.