使用α，ω-二醇作为烷基化试剂合成ω-羟基羧酸和α，ω-二甲基酮。

Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl ketones using alpha,omega-diols as alkylating agents.

机构信息

Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering and High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan.

出版信息

J Org Chem. 2010 Mar 5;75(5):1803-6. doi: 10.1021/jo9027165.

DOI:10.1021/jo9027165

PMID:20121069

Abstract

Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of IrCl(cod) or IrCl(coe)(2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of IrCl(cod) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.

摘要

通过使用α，ω-二醇作为烷基化试剂，在铱催化剂的影响下，成功地合成了ω-羟基羧酸和α，ω-二甲基二酮。例如，在[IrCl（cod）]（2）或[IrCl（coe）]（2）的存在下，用1,13-十三烷二醇对丁基氰基乙酸酯进行烷基化反应，得到了产率良好的丁基 2-氰基-15-羟基十五烷酸酯，该产物易于转化为环十五烷醇内酯（CPDL）。此外，在[IrCl（cod）]（2）和 KOH 的存在下，用 1,10-癸二醇对丙酮进行烷基化反应，得到了产率良好的重要麝香前体 2,15-十六烷二酮（HDDO）。