(Z)-1-phenylthio-2-phenyltelluro-1-hexene

• 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-phenyltelluro-1-hexene
• 英文别名: [(Z)-1-phenylsulfanylhex-1-en-2-yl]tellanylbenzene
• 化学式: C₁₈H₂₀STe
• 分子量: 396.023
• InChiKey: GPOQTCCYEZQLRA-SDXDJHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (Z)-1-phenylthio-2-phenyltelluro-1-hexene 在 正丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.42h， 以63%的产率得到(Z)-1-phenylthio-2-butyl-3-phenyl-3-hydroxy-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
• 作为产物：
  描述：

  联苯二碲 、 苯,(1-己炔基硫代)- 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到(Z)-1-phenylthio-2-phenyltelluro-1-hexene
  参考文献：
  名称：

  Hydrochalcogenation of phenylthioacetylenes. Synthesis of mixed (Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes

  摘要：

  The treatment of 1-phenylthioacetylenes with phenylselenolate and butyl or phenyltellurolate anions generated by the reaction of the corresponding dichalcogenide with NaBH4 in aqueous ethanol results in the formation of mixed 1,2-bis(organylchalcogeno)-1-alkenes of Z configuration. The phenylthio group acts as a directing and activating group for the nucleophilic addition of the chalcogenate anions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02291-7

文献信息

• Hydrochalcogenation of phenylthioacetylenes. Synthesis of mixed (Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes
  作者：Miguel J Dabdoub、Vânia B Dabdoub、Marco A Pereira

  DOI：10.1016/s0040-4039(00)02291-7

  日期：2001.2

  The treatment of 1-phenylthioacetylenes with phenylselenolate and butyl or phenyltellurolate anions generated by the reaction of the corresponding dichalcogenide with NaBH4 in aqueous ethanol results in the formation of mixed 1,2-bis(organylchalcogeno)-1-alkenes of Z configuration. The phenylthio group acts as a directing and activating group for the nucleophilic addition of the chalcogenate anions (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.