(Z)-1-(phenylthio)oct-1-en-3-ol | 89870-30-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-1-(phenylthio)oct-1-en-3-ol
• 英文别名: (Z)-1-phenylsulfanyloct-1-en-3-ol
• CAS: 89870-30-4
• 化学式: C₁₄H₂₀OS
• 分子量: 236.378
• InChiKey: GELAUZCEULRFRA-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-辛炔-3-醇 、 二苯二硫醚 在 copper(l) iodide 、 rongalite 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以90%的产率得到(Z)-1-(phenylthio)oct-1-en-3-ol
  参考文献：
  名称：

  Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of (Z)-1-alkenyl sulfides and selenides

  摘要：

  A simple, stereoselective and efficient method for the hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide has been developed. In the presence of Cul, rongalite, and Cs2CO3, a variety Of disulfides Underwent the reaction of terminal alkynes stereoselectively to afford the corresponding (Z)-1-alkenyl sulfides in moderate to excellent yields. it is noteworthy that hydroselenations of 1,2-diphenyldiselane with alkynes are also conducted smoothly to afford (Z)-1-alkenyl selenides in good yields under the standard conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.022

文献信息

• Conversion of α acetylenic alcohols into αβ unsaturated aldehydes
  作者：Marc Julia、Christian Lefebvre

  DOI：10.1016/s0040-4039(00)99836-8

  日期：1984.1

  Very mild conditions have been found for the efficient regioselective addition of phenylthiol to ethynyl carbinols. A biphasic aqueous acid hydrolysis then leads to α,β-unsaturated aldehydes. The Meyer-Schuster rearrangement is thus brought about in two steps.

  已经发现非常温和的条件可以将苯硫醇有效地区域选择性地加成到乙炔基甲醇中。然后两相水溶液酸水解产生α，β-不饱和醛。因此，迈耶-舒斯特（Meyer-Schuster）重排分两个步骤进行。
• Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of (Z)-1-alkenyl sulfides and selenides
  作者：Zhang-Lin Wang、Ri-Yuan Tang、Pei-Song Luo、Chen-Liang Deng、Ping Zhong、Jin-Heng Li

  DOI：10.1016/j.tet.2008.09.022

  日期：2008.11

  A simple, stereoselective and efficient method for the hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide has been developed. In the presence of Cul, rongalite, and Cs2CO3, a variety Of disulfides Underwent the reaction of terminal alkynes stereoselectively to afford the corresponding (Z)-1-alkenyl sulfides in moderate to excellent yields. it is noteworthy that hydroselenations of 1,2-diphenyldiselane with alkynes are also conducted smoothly to afford (Z)-1-alkenyl selenides in good yields under the standard conditions. (C) 2008 Elsevier Ltd. All rights reserved.