3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester

Base Information

• Chemical Name: 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester
• CAS No.: 405266-59-3
• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.365

Synonyms:3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester

Chemical Property of 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester

Chemical Property:

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Technology Process of 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester

There total 2 articles about 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-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: 88.0%

cyclohexen-3-one-1-carboxylic acid (24079-79-6) + (S)-3-butenyl mandelate (405266-54-8) → 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester (405266-59-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo001631e

Reference yield:

(S)-Mandelic acid (17199-29-0) → 3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester (405266-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / tetracyanoethylene / acetonitrile / 72 h / 50 °C

2: 88 percent / DMAP; DCC / CH₂Cl₂ / 0 - 20 °C

With dmap; ethenetetracarbonitrile; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1021/jo001631e

Reference yield: 62.0%

3-Oxo-cyclohex-1-enecarboxylic acid (S)-but-3-enyloxycarbonyl-phenyl-methyl ester (405266-59-3) → (1R,4S,9S,11R)-4-phenyl-3,6-dioxatricyclo[9.4.0.01,9]pentadecane-2,5,12-trione

Guidance literature:

In dichloromethane; at 20 ℃; UV-irradiation;

DOI:10.1021/jo001631e

upstream raw materials:

cyclohexen-3-one-1-carboxylic acid

(S)-3-butenyl mandelate

(S)-Mandelic acid

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