(R)-hex-5-en-1-yn-3-ylcyclohexane

Base Information

• Chemical Name: (R)-hex-5-en-1-yn-3-ylcyclohexane
• CAS No.: 1378870-78-0
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.275
• Mol file: 1378870-78-0.mol

Synonyms:(R)-hex-5-en-1-yn-3-ylcyclohexane

Chemical Property of (R)-hex-5-en-1-yn-3-ylcyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-hex-5-en-1-yn-3-ylcyclohexane

There total 5 articles about (R)-hex-5-en-1-yn-3-ylcyclohexane 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%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + (S)-1-cyclohexyl-2-propyn-1-ol acetate (108104-21-8) → (R)-hex-5-en-1-yn-3-ylcyclohexane (1378870-78-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; cesium fluoride; In tetrahydrofuran; at 60 ℃; for 14h; regioselective reaction; Inert atmosphere; sealed tube;

DOI:10.1021/ja302329f

Reference yield:

1-cyclohexylprop-2-yn-1-yl acetate (108104-21-8,16169-86-1) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → (R)-1-cyclohexylprop-2-yn-1-yl acetate (936638-45-8) + (R)-hex-5-en-1-yn-3-ylcyclohexane (1378870-78-0) + (S)-hex-5-en-1-yn-3-ylcyclohexane + (S)-1-cyclohexyl-2-propyn-1-ol acetate (108104-21-8)

Guidance literature:

With [(R)-(+)-2,2'-Bis(di-2-furanylphosphino)-6,6'-dimethoxy-1,1'-biphenyl]palladium(II) dichloride; cesium fluoride; In tetrahydrofuran; at 60 ℃; for 14h; Sealed tube; Inert atmosphere;

DOI:10.1002/adsc.201300720

Reference yield:

1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-one (53724-05-3) → (R)-hex-5-en-1-yn-3-ylcyclohexane (1378870-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / Inert atmosphere

1.2: Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; cesium fluoride / tetrahydrofuran / 14 h / 60 °C / Inert atmosphere; sealed tube

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dimethylsulfide borane complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; cesium fluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja302329f

upstream raw materials:

1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-one

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(S)-1-cyclohexyl-2-propyn-1-ol acetate

(1S)-1-cyclohexyl-2-propyn-1-ol

Downstream raw materials:

(S)-hexa-1,5-dien-3-ylcyclohexane

Refernces

• 1、 Ardolino, Michael J.,Morken, James P.. "Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings". . p. 8770 - 8773. Retrieved 2012/07/02.