ethyl (E)-4-phenylbut-1-ene-1-sulfonate | 1002105-77-2

• 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: ethyl (E)-4-phenylbut-1-ene-1-sulfonate
• 英文别名: (E)-ethyl 4-phenylbut-1-ene-1-sulfonate
• CAS: 1002105-77-2
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: MVKZTCMCROHRCA-YRNVUSSQSA-N

物化性质

• 沸点：
  388.5±35.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-phenylbut-1-ene-1-sulfonate 在 四丁基碘化铵 、 difluoro-4-morpholinylsulfonium tetrafluoroborate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 以17%的产率得到
  参考文献：
  名称：

  通过碳硫键裂解，由2-取代的乙磺酰氟立体选择性地构建腈取代的环丙烷

  摘要：

  描述了2-芳基和2-苯乙烯基取代的乙磺酰氟与活性含氰基亚甲基化合物的分子间环丙烷化。该反应通过在无金属条件下进行碳硫键裂解而进行，产率高达99％，从而提供了具有高非对映选择性的各种腈取代的环丙烷。

  DOI：

  10.1002/adsc.201900635
• 作为产物：
  描述：

  苯丙醛 、 ethyl (diethoxyphosphoryl)methanesulfonate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.25h， 以82%的产率得到ethyl (E)-4-phenylbut-1-ene-1-sulfonate
  参考文献：
  名称：

  Synthesis of Natural Product-Inspired Inhibitors of Mycobacterium tuberculosis Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase

  摘要：

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.

  DOI：

  10.1021/jm070669h

文献信息

• Synthesis of Natural Product-Inspired Inhibitors of <i>Mycobacterium tuberculosis</i> Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase
  作者：Belhu B. Metaferia、Brandon J. Fetterolf、Syed Shazad-ul-Hussan、Matthew Moravec、Jeremy A. Smith、Satyajit Ray、Maria-Teresa Gutierrez-Lugo、Carole A. Bewley

  DOI：10.1021/jm070669h

  日期：2007.12.13

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.
• Stereoselective Construction of Nitrile‐Substituted Cyclopropanes from 2‐Substituted Ethenesulfonyl Fluorides <i>via</i> Carbon‐Sulfur Bond Cleavage
  作者：Hao Liu、Balakrishna Moku、Fei Li、Jiabing Ran、Jinsong Han、Sihui Long、Gao‐Feng Zha、Hua‐Li Qin

  DOI：10.1002/adsc.201900635

  日期：2019.10.8

  The intermolecular cyclopropanation of 2‐aryl and 2‐styryl substituted ethenesulfonyl fluorides with active cyano‐containing methylene compounds was described. This reaction proceeds via carbon‐sulfur bond cleavage under metal‐free conditions in up to 99% yield, affording a variety of nitrile‐substituted cyclopropanes with high diastereoselectivity.

  描述了2-芳基和2-苯乙烯基取代的乙磺酰氟与活性含氰基亚甲基化合物的分子间环丙烷化。该反应通过在无金属条件下进行碳硫键裂解而进行，产率高达99％，从而提供了具有高非对映选择性的各种腈取代的环丙烷。