1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene

Base Information

• Chemical Name: 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene
• CAS No.: 286967-32-6
• Molecular Formula: C₁₉H₃₀OSi
• Molecular Weight: 302.532
• Mol file: 286967-32-6.mol

Synonyms:1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene

Chemical Property of 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene

There total 8 articles about 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene 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: 60.0%

chloro-trimethyl-silane (75-77-4) + (R)-5-methyl-cyclohex-2-enone (54307-74-3,15466-88-3) + S-(-)-1-bromo-2-phenylpropane (147514-19-0) → 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene (286967-32-6)

Guidance literature:

S-(-)-1-bromo-2-phenylpropane; With magnesium;

chloro-trimethyl-silane; (R)-5-methyl-cyclohex-2-enone; With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 3h; Further stages.;

DOI:10.1021/ja000239f

Reference yield:

(3R)-3-methylcyclohexanone (13368-65-5) → 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene (286967-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 30 percent / Br₂ / H₂O / 20 °C

2.1: ehtylene glycol; p-toluenesulfonic acid / benzene / 6 h

2.2: 70 percent / NaOH / methanol / 72 h

3.1: Mg

3.2: 60 percent / CuBr(Me₂S); HMPA / tetrahydrofuran / 3 h / -78 °C

With bromine; toluene-4-sulfonic acid; magnesium; ethylene glycol; In water; benzene; 1.1: Bromination / 2.1: Dehydrobromination / 2.2: Dehydrobromination / 3.1: Grignard reaction / 3.2: Addition;

DOI:10.1021/ja000239f

Reference yield:

(S)-2-phenyl-1-propanol (37778-99-7) → 1-trimethylsilyloxy-3(S)-[2(S)-phenyl-1-propyl]-5-(R)-methyl-1-cyclohexene (286967-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.1: 93 percent / LiBr; N,N-dimethylformamide / 3 h / 20 - 70 °C / Heating

3.1: Mg

3.2: 60 percent / CuBr(Me₂S); HMPA / tetrahydrofuran / 3 h / -78 °C

With magnesium; triethylamine; N,N-dimethyl-formamide; lithium bromide; In dichloromethane; 1.1: Addition / 2.1: Bromination / 3.1: Grignard reaction / 3.2: Addition;

DOI:10.1021/ja000239f

upstream raw materials:

chloro-trimethyl-silane

(R)-5-methyl-cyclohex-2-enone

S-(-)-1-bromo-2-phenylpropane

(3R)-3-methylcyclohexanone