S-methoxycarbonylmethyl benzothioate | 6398-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-methoxycarbonylmethyl benzothioate
• 英文别名: methyl 2-(benzoylthio)acetate；S-Benzoyl-thioglykolsaeuremethylester；Methyl 2-benzoylsulfanylacetate
• CAS: 6398-72-7
• 化学式: C₁₀H₁₀O₃S
• 分子量: 210.254
• InChiKey: MQDXXUZXJVUTIA-UHFFFAOYSA-N

物化性质

• 沸点：
  148 °C(Press: 1.2 Torr)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酸 在 五氟吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 S-methoxycarbonylmethyl benzothioate
  参考文献：
  名称：

  五氟吡啶 (PFP​​) 介导的一锅酯和硫酯形成

  摘要：

  酰氟是有价值的合成中间体，但在某些情况下，由于它们易于降解，它们可能难以处理且难以分离。此外，许多用于制备酰氟的试剂与原位生成策略不相容，并且需要在发生任何进一步反应之前分离酰氟。这些因素的结合意味着酰氟目前正在亲核取代过程中进行研究，并且在使用它们的地方通常只能耐受有限的底物范围。在此，我们报道五氟吡啶可用于在温和条件下原位生成酰氟，并且它们随后可用于生成一系列酯和硫酯。该方法提供了直接从母体羧酸简单地一锅合成酯和硫酯的方法。

  DOI：

  10.1039/d2ob01268e

文献信息

• Variant LovD polypeptide
  申请人：The Regents of the University of California

  公开号：US10246689B2

  公开（公告）日：2019-04-02

  The invention disclosed herein relates to methods and materials for producing simvastatin and related compounds such as huvastatin. In particular, the disclosure teaches that variants of the LovD acyltransferase polypeptide can be engineered to exhibit properties that facilitate their use in the production of simvastatin and/or huvastatin. The materials and processes disclosed herein are designed so that fermentation facilities lovastatin being converted to simvastatin and related compounds with minimal modifications.

  本发明涉及生产辛伐他汀和相关化合物（如胡伐他汀）的方法和材料。特别是，本发明揭示了 LovD酰基转移酶多肽的变体可以被设计成具有便于用于生产辛伐他汀和/或胡伐他汀的特性。本文所公开的材料和工艺的设计使发酵设备只需最小的改动即可将洛伐他汀转化为辛伐他汀和相关化合物。
• Method of making variant LovD polypeptides
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US10689628B2

  公开（公告）日：2020-06-23

  The invention disclosed herein relates to methods and materials for producing simvastatin and related compounds such as huvastatin. In particular, the disclosure teaches that variants of the LovD acyltransferase polypeptide can be engineered to exhibit properties that facilitate their use in the production of simvastatin and/or huvastatin. The materials and processes disclosed herein are designed so that fermentation facilitates lovastatin being converted to simvastatin and related compounds with minimal modifications.

  本发明涉及生产辛伐他汀和相关化合物（如胡伐他汀）的方法和材料。特别是，本发明揭示了 LovD酰基转移酶多肽的变体可以被设计成具有有利于生产辛伐他汀和/或胡伐他汀的特性。本文所公开的材料和工艺的设计使发酵有利于将洛伐他汀转化为辛伐他汀和相关化合物，而只需进行最小的改良。
• Methods and materials for making simvastatin and related compounds
  申请人：The Regents of the University of California

  公开号：US10793884B2

  公开（公告）日：2020-10-06

  The invention disclosed herein relates to methods and materials for producing simvastatin and related compounds such as huvastatin.

  本发明涉及生产辛伐他汀和相关化合物（如胡伐他汀）的方法和材料。
• High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides:  Design of Soluble and Insoluble Nucleophile Scavengers
  作者：Joel D. Moore、Robert J. Byrne、Punitha Vedantham、Daniel L. Flynn、Paul R. Hanson

  DOI：10.1021/ol0352759

  日期：2003.11.1

  An efficient strategy for scavenging a host of nucleophiles utilizing an oligomeric bis-acid chloride (OBAC), generated from the ROM polymerization of trans-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyI dichloride, is described. The reactivity and high load of the OBAC reagent is exploited in the scavenging of amines, alcohols, and thiols that are present in excess following a common benzoylation event. Following the scavenging event, these oligomers can be precipitated with EtOAc and filtered (SiO2), leaving benzoylated nucleophiles in excellent yield and purity.
• Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide
  作者：Mieko Arisawa、Tomohiro Kubota、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2008.01.109

  日期：2008.3

  The Wilkinson complex RhCl(PPh3)(3) catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)(3) (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide. (c) 2008 Elsevier Ltd. All rights reserved.