(E)-(4-methylpenta-1,4-dien-1-yl)benzene

Base Information

• Chemical Name: (E)-(4-methylpenta-1,4-dien-1-yl)benzene
• CAS No.: 109898-18-2
• Molecular Formula: C₁₂H₁₄
• Molecular Weight: 158.243
• Mol file: 109898-18-2.mol

Synonyms:(E)-(4-methylpenta-1,4-dien-1-yl)benzene

Chemical Property of (E)-(4-methylpenta-1,4-dien-1-yl)benzene

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of (E)-(4-methylpenta-1,4-dien-1-yl)benzene

There total 24 articles about (E)-(4-methylpenta-1,4-dien-1-yl)benzene 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%

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + (E)-methyl cinnamyl carbonate (87802-71-9,85217-69-2) → (E)-(4-methylpenta-1,4-dien-1-yl)benzene (109898-18-2)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; dicyclohexyl(4-methoxyphenyl)phosphine; triethylsilyl trifluoromethyl sulfonate; triethylamine; In toluene; at 20 ℃; for 3.5h; under 760.051 Torr; regioselective reaction; Inert atmosphere;

DOI:10.1002/asia.201000875

Reference yield: 84.0%

prop-1-en-2-ylzinc(II) chloride (119441-91-7) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-(4-methylpenta-1,4-dien-1-yl)benzene (109898-18-2)

Guidance literature:

(2E)-3-phenyl-2-propen-1-ol; With nickel(II) triflate; 1,2-bis-(diphenylphosphino)ethane; methylzinc chloride; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

prop-1-en-2-ylzinc(II) chloride; In dibutyl ether; toluene; at 120 ℃; for 24h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.6b02564

Reference yield: 80.0%

(3-hydroxypropyl)dimethyl[(E)-2-phenylethen-1-yl]silane + 3-Chloro-2-methylpropene (563-47-3) → (E)-(4-methylpenta-1,4-dien-1-yl)benzene (109898-18-2)

Guidance literature:

With copper(l) iodide; lithium tert-butoxide; triethyl phosphite; In N,N-dimethyl-formamide; at 25 ℃; for 6h; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/anie.201306882

upstream raw materials:

2-methylallyltributyltin

trans-(C₂H₅)3SnCHCHC₆H₅

potassium (E)-trifluoro(styryl)borate

3-Chloro-2-methylpropene

Refernces

• 1、 Tabélé, Clémence,Curti, Christophe,Kabri, Youssef,Primas, Nicolas,Vanelle, Patrice. "Cross-coupling synthesis of methylallyl alkenes: Scope extension and mechanistic study". . p. 22890 - 22899. Retrieved 2015.
• 2、 Zhao, Kuo,Knowles, Robert R.. "Contra-Thermodynamic Positional Isomerization of Olefins". supporting information. p. 137 - 144. Retrieved 2022/01/19.