(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester
CAS No.:866606-96-4
Molecular Formula:C₁₆H₂₄O₃
Molecular Weight:264.365
Hs Code.:

Synonyms:(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

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Chemical Property of (5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

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Technology Process of (5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

There total 4 articles about (5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic 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: 82.0%

: (-)-(5S)-5-isopropyl-2-oxocyclohexanecarboxylic acid methyl ester

: 2468-55-5
5-iodopent-1-yne

: 866606-96-4
(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1021/ol051426r

Reference yield:

: 4746-97-8
cyclohexanedione monoethylene ketal

: 866606-96-4
(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60 percent / NaH / dimethylsulfoxide / 16 h / 50 °C

2.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / 7500.6 Torr

2.2: 6.56 g / AcOH; H₂O / tetrahydrofuran / 15 h / 20 °C

3.1: LiCl; n-BuLi; [R-(R*,R*)]-(+)-bis(α-methylbenzyl)amine / tetrahydrofuran; hexane / 0.5 h / -105 °C

4.1: 82 percent / NaH / dimethylformamide / 18 h / 20 °C

With n-butyllithium; hydrogen; (R,R)-N,N-bis-(1-phenylethyl)amine; sodium hydride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 1.1: Wittig olefination;
DOI:10.1021/ol051426r

Reference yield:

: 19620-35-0
8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane

: 866606-96-4
(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / 7500.6 Torr

1.2: 6.56 g / AcOH; H₂O / tetrahydrofuran / 15 h / 20 °C

2.1: LiCl; n-BuLi; [R-(R*,R*)]-(+)-bis(α-methylbenzyl)amine / tetrahydrofuran; hexane / 0.5 h / -105 °C

3.1: 82 percent / NaH / dimethylformamide / 18 h / 20 °C

With n-butyllithium; hydrogen; (R,R)-N,N-bis-(1-phenylethyl)amine; sodium hydride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol051426r