1-(Phenylthio)-2-(phenylseleno)-3-(trimethylsilyl)propane | 137258-87-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(Phenylthio)-2-(phenylseleno)-3-(trimethylsilyl)propane
• 英文别名: Trimethyl[2-(phenylselanyl)-3-(phenylsulfanyl)propyl]silane；trimethyl-(2-phenylselanyl-3-phenylsulfanylpropyl)silane
• CAS: 137258-87-8
• 化学式: C₁₈H₂₄SSeSi
• 分子量: 379.5
• InChiKey: FJTDBSYOBAMQHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 二苯二硫醚 、 烯丙基三甲基硅烷 反应 73.0h， 以51%的产率得到1-(Phenylthio)-2-(phenylseleno)-3-(trimethylsilyl)propane
  参考文献：
  名称：

  A highly selective thioselenation of olefins using disulfide-diselenide mixed system

  摘要：

  A highly selective thioselenation of olefins has been attained by using a disulfide-diselenide mixed system. Upon irradiation through Pyrex with a tungsten lamp in the absence of solvent, the thioselenation of olefins 1 with diphenyl disulfide (2) and diphenyl diselenide (3) takes place to provide 1-(phenylthio)-2-(phenylseleno)alkanes 4 as a sole product in good yields. In the cases of terminal olefins, the thioselenation proceeds regioselectively. The cyclic olefins like cyclopentene and cyclohexene also undergo thioselenation to give corresponding E isomers stereoselectively. The reaction of the conjugate diene with diphenyl disulfide and diphenyl diselenide produces the 1,4-thioselenation adduct in good yield. The excellent regioselectivity observed in the thioselenation of the terminal olefins is due to the higher reactivity of PhS., compared with PhSe., toward carbon-carbon double bonds and the higher capturing ability of (PhSe)2, compared with (PhS)2, toward carbon radicals.

  DOI：

  10.1021/jo00027a021

文献信息

• Ogawa, Akiya; Sonoda, Noboru, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 331 - 332
  作者：Ogawa, Akiya、Sonoda, Noboru

  DOI：——

  日期：——
• A highly selective thioselenation of olefins using disulfide-diselenide mixed system
  作者：Akiya Ogawa、Hiromichi Tanaka、Hiroshi Yokoyama、Ryoichi Obayashi、Kazuyuki Yokoyama、Noboru Sonoda

  DOI：10.1021/jo00027a021

  日期：1992.1

  A highly selective thioselenation of olefins has been attained by using a disulfide-diselenide mixed system. Upon irradiation through Pyrex with a tungsten lamp in the absence of solvent, the thioselenation of olefins 1 with diphenyl disulfide (2) and diphenyl diselenide (3) takes place to provide 1-(phenylthio)-2-(phenylseleno)alkanes 4 as a sole product in good yields. In the cases of terminal olefins, the thioselenation proceeds regioselectively. The cyclic olefins like cyclopentene and cyclohexene also undergo thioselenation to give corresponding E isomers stereoselectively. The reaction of the conjugate diene with diphenyl disulfide and diphenyl diselenide produces the 1,4-thioselenation adduct in good yield. The excellent regioselectivity observed in the thioselenation of the terminal olefins is due to the higher reactivity of PhS., compared with PhSe., toward carbon-carbon double bonds and the higher capturing ability of (PhSe)2, compared with (PhS)2, toward carbon radicals.