2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

Base Information

Chemical Name:2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone
CAS No.:69285-46-7
Molecular Formula:C₂₂H₂₃NO₅
Molecular Weight:381.428
Hs Code.:

Synonyms:2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

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Chemical Property of 2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

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Technology Process of 2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

There total 8 articles about 2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone 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: 97.0%

: methane sulfonate of 6-cyano-2-hexyne-1-ol

: trans-2-carbobenzyloxy-3-carbomethoxycyclopentanone

: 69285-46-7
2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

Guidance literature:: In methanol; 1,2-dimethoxyethane; water; mineral oil; benzene;

Reference yield:

: 14267-92-6
1-chloro-4-pentyne

: 69285-46-7
2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) C₂H₅MgBr / 1.) THF, reflux, 1.5 h, 2.) THF, 25 deg C, 18 h

2: 85 percent / dimethylsulfoxide / 1.5 h / 80 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 0.42 h / -5 °C

4: 1.) NaH / 1.) dimethoxyethane, 25 deg C, 15 min, 2.) dimethoxyethane, reflux, 5 h

With ethylmagnesium bromide; sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00133a029

Reference yield:

: 923-42-2
butane-1,2,4-tricarboxylic acid

: 69285-46-7
2-(6-cyanohex-2-ynyl)-2-(benzyloxycarbonyl)-3-(methoxycarbonyl)cyclopentanone

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / conc. H₂SO₄ / 1,2-dichloro-ethane / 6 h / Heating

2: 70 percent / NaH, methanol / xylene / 0.33 h / 20 - 25 °C

3: 1.25 h / 185 °C

4: 1.) NaH / 1.) dimethoxyethane, 25 deg C, 15 min, 2.) dimethoxyethane, reflux, 5 h

With methanol; sulfuric acid; sodium hydride; In 1,2-dichloro-ethane; xylene;
DOI:10.1021/jo00133a029