1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one

Base Information

• Chemical Name: 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one
• CAS No.: 283592-62-1
• Molecular Formula: C₁₇H₂₂OSi
• Molecular Weight: 270.447
• Mol file: 283592-62-1.mol

Synonyms:1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one

Chemical Property of 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one

There total 2 articles about 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one 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: 85.0%

1,2-propanediene (463-49-0) + cyclopent-1-enecarbonyl chloride (59253-90-6) + dimethyl(phenyl)silyllithium (3839-31-4) → 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one (283592-62-1)

Guidance literature:

dimethyl(phenyl)silyllithium; With CuCN; In tetrahydrofuran; at 0 ℃; for 0.5h;

1,2-propanediene; In tetrahydrofuran; at -40 - 0 ℃; for 1.5h;

cyclopent-1-enecarbonyl chloride; In tetrahydrofuran; at -40 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00129-0

Reference yield:

1,2-propanediene (463-49-0) + cyclopent-1-enecarbonyl chloride (59253-90-6) + phenyldimethylsilyl chloride (768-33-2) → 1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one (283592-62-1)

Guidance literature:

Multistep reaction;

Reference yield:

1-(cyclopent-1-en-1-yl)-2-dimethyl(phenyl)silylmethylprop-2-en-1-one (283592-62-1) → [1S*,3R*,5S*]-3-[2-dimethyl(phenyl)silylmethylprop-2-en-1-yl]bicyclo[3.3.0]octan-2-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / TFA / tetrahydrofuran / 2.5 h / 0 - 20 °C

2.1: CuCN / tetrahydrofuran / 0.5 h / 0 °C

2.2: tetrahydrofuran / 1 h / -40 °C

2.3: 82 percent / BF₃*Et₂O / tetrahydrofuran / 1.5 h / -40 - 0 °C

With trifluoroacetic acid; In tetrahydrofuran; 1.1: Directed Nazarov reaction / 2.1: Transmetallation / 2.2: Silylcupration / 2.3: Substitution;

DOI:10.1016/S0040-4020(00)00129-0

upstream raw materials:

1,2-propanediene

cyclopent-1-enecarbonyl chloride

dimethyl(phenyl)silyllithium

phenyldimethylsilyl chloride