4,6-Bis(phenylseleno)thianthrene 5-oxide | 135489-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 英文名称: 4,6-Bis(phenylseleno)thianthrene 5-oxide
• 英文别名: 4,6-bis(phenylselanyl)thianthrene 5-oxide
• CAS: 135489-42-8
• 化学式: C₂₄H₁₆OS₂Se₂
• 分子量: 542.442
• InChiKey: MTIYFVYNBCXACO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,6-Bis(phenylseleno)thianthrene 5-oxide 在 苯基溴化镁 、 copper dichloride 作用下， 生成 1,9-Bis(phenylseleno)dibenzothiophene
  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：

  噻蒽 5-氧化物 、 二苯基二硒醚 在 lithium diisopropyl amide 作用下， 生成 4-phenylselanylthianthrene 5-oxide 、 4,6-Bis(phenylseleno)thianthrene 5-oxide
  参考文献：
  名称：

  A Convenient Preparation of Sterically Crowded 1,9-Disubstituted Dibenzothiophenes and 3,3'-Disubstituted Diaryl Sulfides

  摘要：

  Thianthrene-5-oxide (1) reacted with 2.2 equivalents of lithium diisopropylamide to give 4,6-dilithiated 1 which was converted to 4,6-disubstituted thianthrene-5-oxides (3). 3 afforded sterically crowded 1,9-disubstituted dibenzothiophenes (4) in moderate yields on treatment with n-butyllithium or phenyllithium.

  DOI：

  10.3987/com-91-5683