1,2-diphenyl-2,2-di-thiophen-2-yl-ethanone | 54364-07-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenyl-2,2-di-thiophen-2-yl-ethanone
• 英文别名: 1,2-diphenyl-2,2-di-[2]thienyl-ethanone；1,2-Diphenyl-2,2-di-[2]thienyl-aethanon；1,2-Diphenyl-2,2-dithien-2-ylethanone；1,2-diphenyl-2,2-dithiophen-2-ylethanone
• CAS: 54364-07-7
• 化学式: C₂₂H₁₆OS₂
• 分子量: 360.5
• InChiKey: GVQVLLOYJKBDHA-UHFFFAOYSA-N

物化性质

• 沸点：
  510.1±45.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  噻吩 、 联苯甲酰 在 氯仿 、 硫酸 作用下， 生成 1,2-diphenyl-2,2-di-thiophen-2-yl-ethanone
  参考文献：
  名称：

  Steinkopf; Hanske, Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 238,257

  摘要：

  DOI：

文献信息

• Photoreaction between 2-Benzoylthiophene and Phenol or Indole
  作者：Julia Pérez-Prieto、Francisco Boscá、Raquel E. Galian、Agustín Lahoz、Luis R. Domingo、Miguel A. Miranda

  DOI：10.1021/jo034225e

  日期：2003.6.1

  Laser flash photolysis, density functional theory (DFT) calculations, and product studies have been performed to understand the mechanism of photoreduction of 2-benzoylthiophene (BT) in the presence of phenol or indole. Time-resolved experiments showed that BT ketyl (BTH) and phenoxy (PhO) or indolyl (In) radicals are generated with high rate constants and quantum yields close to 1. However, low conversions (specially in the case of indole) of the starting reagents are obtained upon prolonged lamp irradiation, indicating that recombination within the radical pairs must occur to a large extent, regenerating the starting materials. The solvent-dependence of the quenching rate constants, together with DFT theoretical studies, indicate fundamental differences between the mechanisms of the reaction of BT triplet with phenol and indole. Thus, data for phenol agree with the involvement of a hydrogen-bonded exciplex BT HOPh, where concerted electron and proton transfer leads to the (BTHOPh)-O-... radical pair. However, in the case of indole, electron transfer at the (BTHIn)-H-... stage precedes proton transfer. Finally, C-C cross-coupling products have been isolated and characterized in the preparative irradiation of BT in the presence of phenol and indole. The structures of the products have been confirmed by alternative synthesis.
• Steinkopf; Hanske, Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 238,257
  作者：Steinkopf、Hanske

  DOI：——

  日期：——