2-(Phenylthio)-1-(phenylseleno)-1-butoxyethane | 137258-88-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(Phenylthio)-1-(phenylseleno)-1-butoxyethane
• 英文别名: (2-butoxy-2-phenylselanylethyl)sulfanylbenzene
• CAS: 137258-88-9
• 化学式: C₁₈H₂₂OSSe
• 分子量: 365.398
• InChiKey: ZDIOVPKPFNAALL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  乙烯基正丁醚 、 二苯二硫醚 在 二苯基二硒醚 作用下， 反应 20.0h， 以41%的产率得到2-(Phenylthio)-1-(phenylseleno)-1-butoxyethane
  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

• Diphenyl Diselenide-Assisted Radical Addition Reaction of Diphenyl Disulfide to Unsaturated Bonds upon Photoirradiation
  作者：Yuki Yamamoto、Qiqi Chen、Akiya Ogawa

  DOI：10.3390/molecules28062450

  日期：——

  unsaturated compounds. In this study, by combining an interelement compound with homologous heteroatom compounds as a catalyst, we succeeded in suppressing the polymerization of the unsaturated compounds and in attaining a highly selective carbon-heteroatom bond formation through the desired addition reaction. In this paper, we have examined in detail whether such a "catalytic radical reaction" proceeds

  具有杂原子-杂原子单键的元素间化合物在光辐照下与不饱和键的加成反应是高效、原子经济地构建碳-杂原子键的重要方法。然而，在实践中，由于所需的加成反应效率低或不饱和化合物优先聚合，有时无法按预期进行所需的加成反应。在这项研究中，通过将元素间化合物与同系杂原子化合物结合作为催化剂，我们成功地抑制了不饱和化合物的聚合，并通过所需的加成反应实现了高选择性的碳-杂原子键形成。在本文中，我们详细研究了这种“催化自由基反应”是否 对不饱和化合物进行研究，发现一些不饱和化合物（即乙烯基醚、苯乙烯和异氰化物）的二硫醇化可以在 (PhSe)2 的帮助下在光照下进行。作为碳-杂原子键形成的原子经济方法，本研究中开发的方法有望在自由基化学、杂原子化学、合成有机化学和催化剂化学领域产生重大影响。
• 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：——