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在氟仿/叔丁醇钾/三甘醇二甲醚体系下通过酯的亲核三氟甲基化反应合成三氟甲基酮

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system.

作者信息

Fujihira Yamato, Liang Yumeng, Ono Makoto, Hirano Kazuki, Kagawa Takumi, Shibata Norio

机构信息

Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan.

Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan.

出版信息

Beilstein J Org Chem. 2021 Feb 12;17:431-438. doi: 10.3762/bjoc.17.39. eCollection 2021.

Abstract

A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at -40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.

摘要

开发了一种直接的方法,该方法能够使用强效温室气体氟仿(HCF,HFC-23)从容易获得的甲酯形成具有生物吸引力的三氟甲基酮。在-40°C下,氟仿和KHMDS在三甘醇二甲醚中的组合对这种转化有效,产率高达92%。对芳香族、脂肪族和共轭甲酯的三氟甲基化反应的底物范围进行了探索。这项研究提出了一种直接的三氟甲基化过程,可将各种甲酯良好地转化为相应的三氟甲基酮。还探索了各种药效基团在反应条件下的耐受性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a55/7884878/c3d18548a6ee/Beilstein_J_Org_Chem-17-431-g003.jpg

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