3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

Base Information

Chemical Name:3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester
CAS No.:627461-30-7
Molecular Formula:C₂₀H₂₂O₃
Molecular Weight:310.393
Hs Code.:

Synonyms:3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

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Chemical Property of 3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

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Technology Process of 3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

There total 5 articles about 3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester 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: 60.0%

: 627461-28-3
3-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-ylethynyl]-benzoic acid methyl ester

: 627461-30-7
3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

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

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

Reference yield:

: 107658-28-6
methyl 3-(trifluoromethylsulfonyloxy)benzoate

: 627461-30-7
3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 67 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 80 °C

2.1: HF / 2 h / 20 °C

2.2: 60 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

: 627461-30-7
3-((1S,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-ylethynyl)-benzoic acid methyl ester

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

4.1: HF / 2 h / 20 °C

4.2: 60 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