(Z)-1-phenylthio-2-phenylseleno-3-methoxy-1-propene | 1251831-15-8

• 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-2-phenylseleno-3-methoxy-1-propene
• 英文别名: [(Z)-3-methoxy-2-phenylselanylprop-1-enyl]sulfanylbenzene
• CAS: 1251831-15-8
• 化学式: C₁₆H₁₆OSSe
• 分子量: 335.328
• InChiKey: ZSHYINLZGRSHAE-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-phenylsulphenyl-2-methoxymethylethyne 、 苯基锂 在 selenium 、 水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 4.0h， 以70%的产率得到(Z)-1-phenylthio-2-phenylseleno-3-methoxy-1-propene
  参考文献：
  名称：

  One-pot synthesis of mixed ( )-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates

  摘要：

  One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.112

文献信息

• One-pot synthesis of mixed ( )-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Marco A. Pereira、Adriano C.M. Baroni、Francisco A. Marques、Paulo R. de Oliveira、Palimécio G. Guerrero

  DOI：10.1016/j.tetlet.2010.07.112

  日期：2010.9

  One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.