1,9-bis(phenylthio)dibenzoselenophene | 142371-47-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,9-bis(phenylthio)dibenzoselenophene
• 英文别名: 1,9-Bis(phenylsulfanyl)dibenzoselenophene
• CAS: 142371-47-9
• 化学式: C₂₄H₁₆S₂Se
• 分子量: 447.483
• InChiKey: SUVMUIJZFAWCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  27
• 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：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,9-bis(phenylthio)dibenzoselenophene 以 苯 为溶剂， 反应 12.0h， 以77%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：

  Dibenzo<1,2>diselenine 在 苯基锂 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1,9-bis(phenylthio)dibenzoselenophene
  参考文献：
  名称：

  Kimura, Takeshi; Ishikawa, Yasuhiro; Minoshima, Yoshihiro, Heterocycles, 1994, vol. 37, # 1, p. 541 - 552

  摘要：

  DOI：

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。
• The First Preparation and Structures of Dibenzo[<i>bc</i>,<i>fg</i>][1,4]-diselenapentalene and -selenathiapentalene
  作者：Takeshi Kimura、Yasuhiro Ishikawa、Naomichi Furukawa

  DOI：10.1246/cl.1993.635

  日期：1993.4

  Dibenzodiselenapentalene and dibenzoselenathiapentalene were prepared by thermolysis of 1,9-disubstituted dibenzoselenophenes and their structures were determined by X-ray crystallographic analysis.

  Dibenzodiselenapentalene 和dibenzoselenathiapentalene 是通过热解1,9-二取代的dibenzoselenophenes 制备的，并通过X 射线晶体学分析确定了它们的结构。
• Kimura, Takeshi; Ishikawa, Yasuhiro; Furukawa, Naomichi, Heterocycles, 1993, vol. 35, # 1, p. 53 - 56
  作者：Kimura, Takeshi、Ishikawa, Yasuhiro、Furukawa, Naomichi

  DOI：——

  日期：——
• 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.
• Kimura, Takeshi; Ishikawa, Yasuhiro; Minoshima, Yoshihiro, Heterocycles, 1994, vol. 37, # 1, p. 541 - 552
  作者：Kimura, Takeshi、Ishikawa, Yasuhiro、Minoshima, Yoshihiro、Furaukawa, Naomichi

  DOI：——

  日期：——