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氯硫代甲酸甲酯作为硫代酯合成的便捷试剂。

Methyl chlorothioformate as a convenient reagent for thionoester synthesis.

作者信息

Pashko Mykhailo O, Pashkov Kiril V, Granat Dmitriy S, Yagupolskii Yurii L, Ryabukhin Serhiy V, Volochnyuk Dmytro M

机构信息

Enamine Ltd 78 Winston Churchill str. 02094 Kyiv Ukraine

Institute of Organic Chemistry, National Academy of Sciences of Ukraine 5 Akademik Kuhar str. 02660 Kyiv Ukraine.

出版信息

RSC Adv. 2025 May 8;15(19):15116-15120. doi: 10.1039/d5ra01538c. eCollection 2025 May 6.

DOI:10.1039/d5ra01538c
PMID:40343322
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12060010/
Abstract

A promising reagent for introducing the methyl thionoester function into organic molecules through a straightforward synthetic sequence based on common magnesium organics is proposed. A scalable procedure for its production is elaborated. The potential of the reaction, along with its advantages/simplicity, convenience, and effectiveness, is demonstrated and discussed.

摘要

本文提出了一种有前景的试剂,可通过基于常见有机镁化合物的直接合成序列将甲硫代酯官能团引入有机分子中。详细阐述了其可扩展的制备方法。论证并讨论了该反应的潜力及其优势,包括简单性、便利性和有效性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/ac2f5cb89b52/d5ra01538c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/694c2b6efe43/d5ra01538c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/23824464fb59/d5ra01538c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/771f5411a664/d5ra01538c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/ac2f5cb89b52/d5ra01538c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/694c2b6efe43/d5ra01538c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/23824464fb59/d5ra01538c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/771f5411a664/d5ra01538c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41c2/12060010/ac2f5cb89b52/d5ra01538c-s3.jpg

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本文引用的文献

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Photocatalytic O- to S-Rearrangement of Tertiary Cyclopropanols.叔环丙醇的光催化氧到硫的重排反应
Angew Chem Int Ed Engl. 2024 Apr 22;63(17):e202402912. doi: 10.1002/anie.202402912. Epub 2024 Mar 20.
2
Esterification of Thioamides via Selective N-C(S) Cleavage under Mild Conditions.温和条件下通过选择性N-C(S)裂解实现硫代酰胺的酯化反应
Org Lett. 2023 Aug 25;25(33):6149-6154. doi: 10.1021/acs.orglett.3c02238. Epub 2023 Aug 14.
3
An efficient and straightforward approach for accessing thionoesters palladium-catalyzed C-N cleavage of thioamides.
一种高效、直接的方法,用于通过钯催化硫代酰胺的 C-N 裂解来制备硫代酸酯。
Org Biomol Chem. 2022 Feb 16;20(7):1532-1537. doi: 10.1039/d1ob02349g.
4
Ni-Catalyzed Synthesis of Thiocarboxylic Acid Derivatives.镍催化的硫代羧酸衍生物合成。
Org Lett. 2022 Jan 21;24(2):619-624. doi: 10.1021/acs.orglett.1c04074. Epub 2022 Jan 3.
5
Preparation and reactions of polyfunctional magnesium and zinc organometallics in organic synthesis.有机合成中多官能团有机镁和有机锌化合物的制备及反应
Chem Sci. 2021 Mar 16;12(17):6011-6019. doi: 10.1039/d1sc00685a.
6
Ynamide-Mediated Thionoester and Dithioester Syntheses.ynamide介导的硫代酯和二硫代酯合成。
Org Lett. 2020 Aug 21;22(16):6628-6631. doi: 10.1021/acs.orglett.0c02402. Epub 2020 Aug 11.
7
A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride.使用氟化银从硫代酯便捷合成二氟烷基醚
Chemistry. 2019 Dec 13;25(70):15993-15997. doi: 10.1002/chem.201904132. Epub 2019 Nov 7.
8
Base-Catalyzed Transesterification of Thionoesters.硫代酯的碱催化酯交换反应
J Org Chem. 2018 Oct 19;83(20):12784-12792. doi: 10.1021/acs.joc.8b02260. Epub 2018 Oct 4.
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Thionoesters: A Native Chemical Ligation-Inspired Approach to Cysteine-Triggered HS Donors.硫酮酯:一种受天然化学连接启发的半胱氨酸触发 HS 供体的方法。
J Am Chem Soc. 2018 Oct 3;140(39):12574-12579. doi: 10.1021/jacs.8b07268. Epub 2018 Sep 19.
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Chemistry. 2018 Apr 20;24(23):6062-6066. doi: 10.1002/chem.201800957. Epub 2018 Mar 25.