(E)-1-trimethylsilyl-1-nonen-3-yne

Base Information

• Chemical Name: (E)-1-trimethylsilyl-1-nonen-3-yne
• CAS No.: 120501-74-8
• Molecular Formula: C₁₂H₂₂Si
• Molecular Weight: 194.392
• Mol file: 120501-74-8.mol

Synonyms:(E)-1-trimethylsilyl-1-nonen-3-yne

Chemical Property of (E)-1-trimethylsilyl-1-nonen-3-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-trimethylsilyl-1-nonen-3-yne

There total 2 articles about (E)-1-trimethylsilyl-1-nonen-3-yne 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: 78.0%

(2-bromovinyl)trimethylsilane (41309-43-7,70737-20-1,13682-94-5) + 1-heptynylzinc chloride (64146-57-2) → (E)-1-trimethylsilyl-1-nonen-3-yne (120501-74-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)86721-0

Reference yield:

1-Heptyne (628-71-7) + (2-bromovinyl)trimethylsilane (41309-43-7,70737-20-1,13682-94-5) → (cis-2-bromo-vinyl)-trimethyl-silane (70737-20-1) + (E)-1-trimethylsilyl-1-nonen-3-yne (120501-74-8)

Guidance literature:

With ethylmagnesium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1.) THF, 65 deg C, 1 h, -20 deg C, 0.5 h, 2.) THF, 0 deg C, 2 h;

DOI:10.1016/S0040-4020(01)89506-5

Reference yield:

(E)-1-trimethylsilyl-1-nonen-3-yne (120501-74-8) → (2E,4Z)-2,4-decadienal (25152-83-4,65909-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 2-methyl-2-butene, 10 M borane-dimethylsulfide, 2.) acetic acid, 3.) 3N NaOH, 35percent H₂O₂ / 1.) THF, 20 deg C, 3 h, 2.) THF, 60 deg C, 7 h, 3.) 40 deg C, 3.5 h

2: 1.) TiCl₄, 2.) 50percent aq. methanol / 1.) CH₂Cl₂, -78 deg C, 1 h and 20 min, 2.) -20 deg C

With methanol; sodium hydroxide; 2-methyl-but-2-ene; dimethylsulfide borane complex; dihydrogen peroxide; titanium tetrachloride; acetic acid;

DOI:10.1016/S0040-4020(01)89506-5

upstream raw materials:

1-Heptyne

(2-bromovinyl)trimethylsilane

1-heptynylzinc chloride

Downstream raw materials:

(2E,4Z)-2,4-decadienal

Refernces

• 1、 Andreini, Bianca Patrizia,Carpita, Adriano,Rossi, Renzo,Scamuzzi, Barbara. "PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES". . p. 5621 - 5640. Retrieved 2007/10/02.