(E)-S-Phenyl 4,4-dimethylpent-2-enethioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: (E)-S-Phenyl 4,4-dimethylpent-2-enethioate
• 英文别名: S-phenyl (2E)-4,4-dimethyl-2-pentenethioate；S-phenyl (E)-4,4-dimethylpent-2-enethioate
• 化学式: C₁₃H₁₆OS
• 分子量: 220.335
• InChiKey: PUJPBMZGQQYPGJ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙炔基苯基硫醚 在 polyphosphoric acid trimethylsilyl ester 、 乙基溴化镁 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 (E)-S-Phenyl 4,4-dimethylpent-2-enethioate
  参考文献：
  名称：

  Meyer-Schuster Rearrangement of .gamma.-Sulfur-Substituted Propargyl Alcohols: A Convenient Synthesis of .alpha.,.beta.-Unsaturated Thioesters

  摘要：

  gamma-Sulfur-substituted propargyl alcohols 1a-e and 1ij reacted with polyphosphoric acid trimethylsilyl ester (PPSE) to give the alpha,beta-unsaturated thioesters 3a-e and 3ij in good yields. However, the reactions of 3,3-dibutyl-1 -(phenylthio)propargyl alcohol (1k) and 1-(phenylthio)ethynyl- 1-cyclo alkanols 1l-n with PPSE gave the enyne sulfides 2k-n exclusively.

  DOI：

  10.1021/jo00120a024

文献信息

• Regioselective control of the thiocarbonylation of terminal acetylenes with arylthiols catalyzed by Pd(II) and diphosphine ligands
  作者：B El Ali、J Tijani、A El-Ghanam、M Fettouhi

  DOI：10.1016/s0040-4039(00)02169-9

  日期：2001.2

  Control of the regioselective thiocarbonylation of terminal acetylenes 1a-e with arylthiols 2a,b was successfully achieved by using Pd(OAc)(2) and 1,4-bis(diphenylphosphino)butane (dppb), or 1,3-bis(diphenylphosphino)propane (dppp), as catalysts. The formation of the thioesters 3 or 4 depends mainly on the type of ligand (dppp or dppb) and the solvent (THF or CH2Cl2) under CO/H+ or syngas mixture. (C) 2001 Elsevier Science Ltd. All rights reserved.