pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane

Base Information

• Chemical Name: pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane
• CAS No.: 256518-34-0
• Molecular Formula: C₁₉H₃₁BO₂
• Molecular Weight: 302.265
• Mol file: 256518-34-0.mol

Synonyms:pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane

Chemical Property of pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane

There total 1 articles about pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane 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: 55.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene (73395-75-2) → pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane (256518-34-0)

Guidance literature:

With dimethylsulfide borane complex; In dichloromethane; at 0 - 50 ℃;

DOI:10.1016/S0040-4020(99)00962-X

Reference yield: 87.0%

pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane (256518-34-0) → 2-[(1E,3E)-4-iodobuta-1,3-dien-1-yl]-1,3,3-trimethylcyclohex-1-ene (256518-84-0)

Guidance literature:

With sodium methylate; Iodine monochloride; In tetrahydrofuran; methanol; dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4020(99)00962-X

Reference yield:

pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane (256518-34-0) → methyl 9,13-bisdesmethylretinoate (5507-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / MeONa; ICl / methanol; tetrahydrofuran; CH₂Cl₂ / -78 °C

2: 81 percent / Pd₂(dba)3; AsPh₃ / various solvent(s) / 0.5 h / 50 °C

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; sodium methylate; Iodine monochloride; In tetrahydrofuran; methanol; dichloromethane; 1: Substitution / 2: Alkylation;

DOI:10.1016/S0040-4020(99)00962-X

upstream raw materials:

2,3-dimethyl-2,3-butane diol

(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene

Downstream raw materials:

2-[(1E,3E)-4-iodobuta-1,3-dien-1-yl]-1,3,3-trimethylcyclohex-1-ene

methyl 9,13-bisdesmethylretinoate

methyl 9-desmethylretinoate

Refernces