1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate

Base Information

• Chemical Name: 1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate
• CAS No.: 72048-00-1
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• DSSTox Substance ID: DTXSID801173832
• Mol file: 72048-00-1.mol

Synonyms:DTXSID801173832;1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate;72048-00-1

Chemical Property of 1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 274.12050905
• Heavy Atom Count: 20
• Complexity: 391

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1(CC(=C)CC1C2=CC=CC=C2)C(=O)OC

Technology Process of 1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate

There total 5 articles about 1,1-Dimethyl 4-methylene-2-phenyl-1,1-cyclopentanedicarboxylate 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%

dimethyl 2-benzylidenepropanedioate (6626-84-2) + 3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene (74532-54-0) → methyl 1-(methoxycarbonyl)-2-phenyl-4-methylenecyclopentane-1-carboxylate (72048-00-1)

Guidance literature:

tetrakis(triethylphosphite)nickel⁽⁰⁾; In toluene; Heating;

DOI:10.1039/c39860001201

Reference yield: 73.0%

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0) + dimethyl 2-benzylidenepropanedioate (6626-84-2) → methyl 1-(methoxycarbonyl)-2-phenyl-4-methylenecyclopentane-1-carboxylate (72048-00-1)

Guidance literature:

palladium diacetate; triphenylphosphine; In tetrahydrofuran; for 5h; Heating; further catalysts;

DOI:10.1021/ja00346a035

Reference yield: 69.0%

dimethyl 2-benzylidenepropanedioate (6626-84-2) + Benzoic acid 2-trimethylsilanylmethyl-allyl ester (84642-45-5) → methyl 1-(methoxycarbonyl)-2-phenyl-4-methylenecyclopentane-1-carboxylate (72048-00-1)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; for 11h; Heating;

DOI:10.1021/ja00346a035

upstream raw materials:

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane

dimethyl 2-benzylidenepropanedioate

3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene

Benzoic acid 2-trimethylsilanylmethyl-allyl ester

Downstream raw materials:

(2R,4R)-4-Hydroxy-2-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester

(2S,4S)-4-Hydroxy-2-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester