甲基(S)-5-氯-2-羟基-1-氧-2,3-二氢- 1h -茚二酮-2-羧酸酯：(S)-吲哚威的关键中间体，以三必和二必水为氧化剂高效便捷地合成

IF 3.4 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Reaction Chemistry & Engineering Pub Date : 2025-01-06 DOI:10.1039/D4RE00510D

Yun Zhang, Yao Du, Yan-Biao Chen, Jia-Huan Nie, Yue Xiong, Bao-Dong Cui, Xue-Qing Mou, Ming-Qiang Zhou and Yong-Zheng Chen

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引用次数: 0

摘要

茚虫威是一种新型的广谱噻嗪类杀虫剂，活性成分仅为(S)-茚虫威。(S)-5-氯-2-羟基-1-氧-2,3-二氢- 1h -茚-2-羧酸酯是合成(S)-茚虫威的关键中间体。然而，目前生产中间体的工艺不方便，而且难以扩大规模。在此，我们报告了一种高效、高立体选择性和工业上可行的中间体制备方案，其特点是使用叔丁基过氧化氢（thbhp, 70% in H2O）作为氧化剂，过滤净化和温和的条件。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Efficient and convenient synthesis of methyl (S)-5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate: a key intermediate for (S)-indoxacarb using aqueous TBHP as oxidant†

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Efficient and convenient synthesis of methyl (S)-5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate: a key intermediate for (S)-indoxacarb using aqueous TBHP as oxidant†

Indoxacarb is a novel broad-spectrum oxadiazine insecticide, and only (S)-indoxacarb is the active ingredient. (S)-5-Chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate is the key intermediate for synthesising (S)-indoxacarb. However, the current process for producing the intermediate is inconvenient and difficult to scale up. Herein, we report an improved protocol for the efficient, highly stereoselective and industrially feasible preparation of the intermediate, which features the use of tert-butyl hydroperoxide (TBHP, 70% in H₂O) as oxidant, purification by filtration and mild conditions.

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来源期刊

Reaction Chemistry & Engineering Chemistry-Chemistry (miscellaneous)

CiteScore

6.60

自引率

7.70%

发文量

227

期刊介绍： Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society. From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.