(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

Base Information

Chemical Name:(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one
CAS No.:179944-24-2
Molecular Formula:C₁₇H₃₀OSi
Molecular Weight:278.51
Hs Code.:

Synonyms:(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

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Chemical Property of (-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

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Technology Process of (-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

There total 5 articles about (-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one 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: 93.0%

: 1423-60-5
methyl ethynyl ketone

: 179944-23-1
(+)-(4R)-trimethyl[(3,3,4-trimethylcyclohex-1-en-1-yl)methyl]silane

: 179944-24-2
(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

Guidance literature:: With dimethylaluminum chloride; In dichloromethane; at -30 ℃; for 0.333333h;
DOI:10.1021/jo960392l

Reference yield:

: 1423-60-5
methyl ethynyl ketone

: 179944-23-1
(+)-(4R)-trimethyl[(3,3,4-trimethylcyclohex-1-en-1-yl)methyl]silane

: 179944-24-2
(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

: (1'R,3'R,3E)-4-(2',2',3'-trimethyl-(Z)-6'-[(trimethylsilyl)methylidene]cyclohex-1'-yl)but-3-en-2-one

Guidance literature:: With 4 A molecular sieve; zinc(II) iodide; In dichloromethane; at 20 ℃; for 12h; Title compound not separated from byproducts;
DOI:10.1021/jo960392l

Reference yield:

: 89162-97-0
(R)-(+)-3,4-dimethyl-2-cyclohexen-1-one

: 179944-24-2
(-)-(1'R,5'R,3E)-4-(5',6',6'-trimethyl-2'-[(trimethylsilyl)methyl]cyclohex-2'-en-1'-yl)but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: copper(I) cyanide / diethyl ether / 1 h / -30 - -20 °C

1.2: diethyl ether / 1 h / -78 - -30 °C

1.3: 92 percent / hexamethylphosphoric triamide / diethyl ether; tetrahydrofuran / 12 h / -30 - 20 °C

2.1: 85 percent / nickel acetylacetonate / tetrahydrofuran; diethyl ether / 11 h / 20 °C

3.1: ZnI₂

With copper(l) cyanide; bis(acetylacetonate)nickel(II); zinc(II) iodide; In tetrahydrofuran; diethyl ether; 1.1: coordination / 1.2: Addition / 1.3: Esterification / 2.1: Substitution / 3.1: H-ene reaction;
DOI:10.1021/jo960392l