1-(Phenylsulfinyl)-9-(phenylthio)dibenzoselenophene | 142371-52-6

• 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-(Phenylsulfinyl)-9-(phenylthio)dibenzoselenophene
• 英文别名: 1-(Benzenesulfinyl)-9-phenylsulfanyldibenzoselenophene
• CAS: 142371-52-6
• 化学式: C₂₄H₁₆OS₂Se
• 分子量: 463.482
• InChiKey: FBWBDGONLJYZLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Phenylsulfinyl)-9-(phenylthio)dibenzoselenophene 以 苯 为溶剂， 反应 12.0h， 以91%的产率得到triphenyleno<4,5-bcd>selenophene
  参考文献：
  名称：

  Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes

  摘要：

  1,9-Dithia and 1,9-diselena substituents in dibenzochalcogenophenes 1 are in close proximity within the van der Waals S-S and Se-Se contacts and hence have a strong through-space interaction. Photolysis of the compounds 1 with a 400 W high-pressure mercury lamp in benzene produces triphenyleno[4,5-bcd]chalcogenophenes 2 and tribenzo[bc,e,hi][2,7]dichalcogenaazulenes 3 in high yields, except for the dibenzofuran derivative, via photoexcitation, sequential desulfurization or deselenization, and intramolecular cyclization. In the reaction, 1,9-bis(phenylthio)dibenzofuran (1e) exhibits lower reactivity as compared with other dibenzothiophene and dibenzoselenophene derivatives. The X-ray crystallographic analysis of 1,9-bis(phenylseleno)dibenzoselenaphene (1a), 1,9-bis(phenylseleno)dibenzothiophene (1b), and 1,9-bis(phenylthio)dibenzoselenophene (1c) demonstrated that; their structures are distorted as is also that of 1,9-bis(phenylthio)dibenzothiophene (1d),(1) while dibenzofuran derivative 1e was found to be a nearly planar molecule. The structure and reactivity relationship of compounds 1a-e was examined in the photolytic reactions by comparing their interheteroatomic distances at the 1,9 positions and their oxidation potentials. Furthermore, compounds 1a-e afforded the corresponding monosulfoxides and bis-sulfoxides on oxidation with m-chloroperbenzoic acid which were photolyzed readily to give also 2 and 3.

  DOI：

  10.1021/jo00102a043
• 作为产物：
  描述：

  1,9-bis(phenylthio)dibenzoselenophene 在 硫酸 、 水 作用下， 生成 1-(Phenylsulfinyl)-9-(phenylthio)dibenzoselenophene
  参考文献：
  名称：

  通过配体偶联反应制备空间拥挤的 1,9-二苯硒代二苯并在化学和电化学氧化作用下形成新的二氧化硫和二硒代二硒化物

  摘要：

  制备了空间拥挤的 1,9-双(苯硫基)二苯并硒吩 (4a) 和 1,9-双 (苯基硒基) 二苯并硒吩 (4b)。在浓硫酸中，分别从 4a 和 4b 生成新的二硫二甲基亚砜和二硒化二甲苯二甲基亚砜。

  DOI：

  10.1246/cl.1992.675

文献信息

• Preparation of Sterically Congested 1,9-Disubstituted Dibenzoselenophenes by Ligand Coupling Reactions and Formation of New Dithia and Diselena Dications on Chemical and Electrochemical Oxidations
  作者：Naomichi Furukawa、Yasuhiro Ishikawa、Takeshi Kimura、Satoshi Ogawa

  DOI：10.1246/cl.1992.675

  日期：1992.4

  Sterically congested 1,9-bis(phenylthio)dibenzoselenophene (4a) and 1,9-bis(phenylseleno)dibenzoselenophene (4b) were prepared. New dithia dication and diselena dication were generated from 4a and 4b, respectively, in coned sulfuric acid.

  制备了空间拥挤的 1,9-双(苯硫基)二苯并硒吩 (4a) 和 1,9-双 (苯基硒基) 二苯并硒吩 (4b)。在浓硫酸中，分别从 4a 和 4b 生成新的二硫二甲基亚砜和二硒化二甲苯二甲基亚砜。
• Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes
  作者：Takeshi Kimura、Yasuhiro Ishikawa、Kensaku Ueki、Yoji Horie、Naomichi Furukawa

  DOI：10.1021/jo00102a043

  日期：1994.11

  1,9-Dithia and 1,9-diselena substituents in dibenzochalcogenophenes 1 are in close proximity within the van der Waals S-S and Se-Se contacts and hence have a strong through-space interaction. Photolysis of the compounds 1 with a 400 W high-pressure mercury lamp in benzene produces triphenyleno[4,5-bcd]chalcogenophenes 2 and tribenzo[bc,e,hi][2,7]dichalcogenaazulenes 3 in high yields, except for the dibenzofuran derivative, via photoexcitation, sequential desulfurization or deselenization, and intramolecular cyclization. In the reaction, 1,9-bis(phenylthio)dibenzofuran (1e) exhibits lower reactivity as compared with other dibenzothiophene and dibenzoselenophene derivatives. The X-ray crystallographic analysis of 1,9-bis(phenylseleno)dibenzoselenaphene (1a), 1,9-bis(phenylseleno)dibenzothiophene (1b), and 1,9-bis(phenylthio)dibenzoselenophene (1c) demonstrated that; their structures are distorted as is also that of 1,9-bis(phenylthio)dibenzothiophene (1d),(1) while dibenzofuran derivative 1e was found to be a nearly planar molecule. The structure and reactivity relationship of compounds 1a-e was examined in the photolytic reactions by comparing their interheteroatomic distances at the 1,9 positions and their oxidation potentials. Furthermore, compounds 1a-e afforded the corresponding monosulfoxides and bis-sulfoxides on oxidation with m-chloroperbenzoic acid which were photolyzed readily to give also 2 and 3.