phenylethynylthioacetic acid methyl ester | 36814-62-7

• 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: phenylethynylthioacetic acid methyl ester
• 英文别名: methyl 2-(2-phenylethynylsulfanyl)acetate
• CAS: 36814-62-7
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: GJZLVZWQHPZJAS-UHFFFAOYSA-N

物化性质

• 沸点：
  306.4±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  phenylethynylthioacetic acid methyl ester 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 (2-Phenyl-ethinyl-(1))-thio-essigsaeure
  参考文献：
  名称：

  Unsaturated thioacetic acids as novel mechanism-based inhibitors of peptidylglycine α-hydroxylating monooxygenase

  摘要：

  Several unsaturated thioacetic acids were synthesized as potential mechanism-based inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM) prepared from horse serum. Trans-styrylthioacetic acid produced potent time-dependent inhibition of PHM. Potential mechanisms are proposed to explain PHM inactivation by unsaturated thioacetic acids.

  DOI：

  10.1016/0960-894x(96)00041-8
• 作为产物：
  描述：

  4-苯基-1,2,3-噻二唑 、 溴乙酸甲酯 在 正丁基锂 作用下， 生成 phenylethynylthioacetic acid methyl ester
  参考文献：
  名称：

  Unsaturated thioacetic acids as novel mechanism-based inhibitors of peptidylglycine α-hydroxylating monooxygenase

  摘要：

  Several unsaturated thioacetic acids were synthesized as potential mechanism-based inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM) prepared from horse serum. Trans-styrylthioacetic acid produced potent time-dependent inhibition of PHM. Potential mechanisms are proposed to explain PHM inactivation by unsaturated thioacetic acids.

  DOI：

  10.1016/0960-894x(96)00041-8

文献信息

• DIBENZOTHIOPHENE SALT AS ALKYNYLATING AND CYANATING AGENT
  申请人：GEORG-AUGUST-UNIVERSITÄT GÖTTINGEN STIFTUNG ÖFFENTLICHEN RECHTS

  公开号：US20210261519A1

  公开（公告）日：2021-08-26

  The present invention describes a new alkynylation and cyanation agent, as well as its preparation and use to introduce nitrile (cyano) or alkyne groups into chemical target molecules by means of an electrophilic reaction. To enable an electrophilic reaction, the chemical backbone of dibenzothiophene was used.

  本发明描述了一种新的炔基化和氰基化试剂，以及其制备和用途，通过亲电反应将腈基（氰基）或炔基引入化学靶分子中。为了实现亲电反应，使用了二苯并噻吩的化学骨架。
• 5-(Alkynyl)dibenzothiophenium Triflates: Sulfur-Based Reagents for Electrophilic Alkynylation
  作者：Bernd Waldecker、Finn Kraft、Christopher Golz、Manuel Alcarazo

  DOI：10.1002/anie.201807418

  日期：2018.9.17

  The synthesis of a series of 5‐(alkynyl) dibenzothiophenium triflates, prepared from dibenzo[b,d]thiophene 5‐oxide and the corresponding trimethylsilyl‐substituted alkynes is reported. Their structures were determined by X‐ray crystallography, and their reactivities as electrophilic alkynylation reagents evaluated. Their broad substrate scope and functional‐group tolerance illustrate their potential

  据报道，由5-苯并[b，d]噻吩5-氧化物和相应的三甲基甲硅烷基取代的炔烃制备的一系列5-（炔基）二苯并噻吩三氟甲磺酸酯的合成。通过X射线晶体学确定其结构，并评估其作为亲电炔化试剂的反应性。它们广泛的底物范围和功能基团耐受性说明了它们有可能成为广泛使用的EBX试剂的替代品。同位素标记研究表明，炔基二苯并噻吩鎓盐可能会受到亲核试剂在α-或β-碳原子上的攻击，具体取决于其取代方式的性质。随后消除二苯并噻吩单元和其中一个基团的1,2-迁移（如果发生β-进攻）提供了所需的炔烃。
• Reactions of unsaturated sulfides with carbenes. 22. Reactivities of sulfur and double bond, and formation of unsaturated sulfonium ylides
  作者：Wataru Ando、Hirofumi Higuchi、Toshihiko Migita

  DOI：10.1021/jo00441a010

  日期：1977.10