trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne

Base Information

• Chemical Name: trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne
• CAS No.: 82464-38-8
• Molecular Formula: C₁₅H₂₀Si
• Molecular Weight: 228.409
• Mol file: 82464-38-8.mol

Synonyms:trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne

Chemical Property of trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne

There total 13 articles about trans-6-phenyl-1-trimethylsilylhex-3-en-1-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: 96.0%

phenethylmagnesium bromide (3277-89-2) + Trimethyl-((E)-4-phenylsulfanyl-but-3-en-1-ynyl)-silane (161944-19-0) → trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne (82464-38-8)

Guidance literature:

With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1016/S0022-328X(98)00724-4

Reference yield: 68.0%

C15H20OSi → trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne (82464-38-8)

Guidance literature:

With n-butyllithium; zirconocene dichloride; In hexane; toluene; at -20 - 20 ℃; for 1h; stereoselective reaction;

DOI:10.1055/s-0032-1316894

Reference yield: 68.0%

3-phenyl-propionaldehyde (104-53-0) + (3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide (42134-49-6) → trans-6-phenyl-1-trimethylsilylhex-3-en-1-yne (82464-38-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) -72 deg C, 0.75 h, 2.) -70 deg C, 0.5 h;

upstream raw materials:

3-phenyl-propionaldehyde

(3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide

1,1-bis(trimethylsilyl)-2-propyne

phenethylmagnesium bromide

Downstream raw materials:

2-((1E,3E)-6-Phenyl-hexa-1,3-dienyl)-benzo[1,3,2]dioxaborole

4,4,5,5-Tetramethyl-2-((1E,3E)-6-phenyl-hexa-1,3-dienyl)-[1,3,2]dioxaborolane

(E)-hex-3-en-5-yn-1-ylbenzene

methyl trans-6-phenylhex-3-enoate

Refernces

• 1、 Denichoux, Aurélien,Cyklinsky, Mathieu,Chemla, Fabrice,Ferreira, Franck,Pérez-Luna, Alejandro. "Conjugated enyne synthesis by rearrangement of acetylenic epoxides mediated by low-valence organotitanium and organozirconium reagents". . p. 1001 - 1005. Retrieved 2013/06/27.
• 2、 Markó, István E.,Giard, Thierry,Sumida, Shinichi,Gies, Anne-Elisabeth. "Regio- and stereoselective cyclopropanation of functionalised dienes. Novel methodology for the synthesis of vinyl- and divinyl-cyclopropanes". . p. 2317 - 2320. Retrieved 2007/10/03.