(S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene

Base Information

• Chemical Name: (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene
• CAS No.: 1613507-31-5
• Molecular Formula: C₂₁H₂₄
• Molecular Weight: 276.422
• Mol file: 1613507-31-5.mol

Synonyms:

Chemical Property of (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene

There total 3 articles about (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene 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:

triphenylboroxine (3262-89-3) + C20H28O2 (1613507-13-3) → (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene (1613507-31-5) + (R,E)-(3-cyclohexylpent-1-en-1-yl)benzene

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; sodium methylate; benzyldiphenylphosphane; In acetonitrile; at 20 ℃; for 4h; Overall yield = 91 %; Overall yield = 150 mg; stereospecific reaction; Inert atmosphere;

DOI:10.1021/ol5016724

Reference yield:

(2E)-3-cyclohexyl-3-phenylprop-2-en-1-ol (462093-58-9) → (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene (1613507-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 18 h / 23 °C / Inert atmosphere

2.1: hydrogen; C₂₆H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) / tetrahydrofuran / 18 h / 23 °C / Inert atmosphere; Schlenk technique

3.1: nickel diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / tetrahydrofuran; diethyl ether; 2-methyltetrahydrofuran / 24 h / 120 °C / Inert atmosphere; Schlenk technique

With C₂₆H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; nickel diacetate; sodium hydride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In tetrahydrofuran; 2-methyltetrahydrofuran; diethyl ether;

DOI:10.1021/jacs.8b02134

Reference yield:

(E)-(1-cyclohexyl-3-methoxyprop-1-en-1-yl)benzene → (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene (1613507-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; C₂₆H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) / tetrahydrofuran / 18 h / 23 °C / Inert atmosphere; Schlenk technique

2: nickel diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / tetrahydrofuran; diethyl ether; 2-methyltetrahydrofuran / 24 h / 120 °C / Inert atmosphere; Schlenk technique

With C₂₆H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; nickel diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In tetrahydrofuran; 2-methyltetrahydrofuran; diethyl ether;

DOI:10.1021/jacs.8b02134

upstream raw materials:

triphenylboroxine

C₂₀H₂₈O₂

(2E)-3-cyclohexyl-3-phenylprop-2-en-1-ol

Refernces

• 1、 Srinivas, Harathi D.,Zhou, Qi,Watson, Mary P.. "Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines". supporting information. p. 3596 - 3599. Retrieved 2014/07/21.