(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

Base Information

Chemical Name:(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one
CAS No.:627461-26-1
Molecular Formula:C₁₈H₂₀O₂
Molecular Weight:268.356
Hs Code.:

Synonyms:(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

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Chemical Property of (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

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Technology Process of (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

There total 5 articles about (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-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: 70.0%

: 627461-20-5
(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene

: 627461-26-1
(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

Guidance literature:: (1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-phenylethynyl]-7a-methyl-octahydro-indene; With hydrogen fluoride; at 20 ℃; for 2h;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ol0351246

Reference yield:

: 65423-56-5
1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene

: 627461-26-1
(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 53 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

2.1: HF / 2 h / 20 °C

2.2: 70 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / 20 °C

With hydrogen fluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; 1.1: Sonogashira coupling;
DOI:10.1021/ol0351246

Reference yield:

: 140659-43-4
[1S-(1β,4β,7aβ)]-[1R-(3aα)]-octahydro-1-acetyl-4-[(tert-butyldimethylsilyl)oxy]-7a-methyl-1H-indene

: 627461-26-1
(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 64 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

2.1: 98 percent / tetrahydrofuran; hexane / 1 h / 20 °C

3.1: 53 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

4.1: HF / 2 h / 20 °C

4.2: 70 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / 20 °C

With hydrogen fluoride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 3.1: Sonogashira coupling;
DOI:10.1021/ol0351246