1,1-dibenzoyl-2-phenylhydrazine | 136953-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-dibenzoyl-2-phenylhydrazine
• 英文别名: N.N'-Dibenzoyl-phenylhydrazin；Dibenzoylphenylhydrazin；N-benzoyl-N'-phenylbenzohydrazide
• CAS: 136953-42-9
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: TXEZRSZMQKTZBP-UHFFFAOYSA-N

物化性质

• 沸点：
  467.2±28.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  偶氮苯六氟磷酸盐 、 联苯甲酰 在 titanium(III) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 0.67h， 以12%的产率得到2-苯基苯并肼
  参考文献：
  名称：

  Addition of semidione radicals to arenediazonium ions: synthesis of 1,1-diacyl-2-arylhydrazines

  摘要：

  The alpha-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET). When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5). A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.

  DOI：

  10.1021/jo00024a021

文献信息

• Insecticidal N'-substituted-N-alkylcarbonyl-N'-acyl hydrazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0232075B1

  公开（公告）日：1991-03-13
• Insecticidal N'-substituted-N-acyl-N'-alkylcarbonylhydrazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0234944B1

  公开（公告）日：1991-04-10
• US5225443A
  申请人：——

  公开号：US5225443A

  公开（公告）日：1993-07-06
• Addition of semidione radicals to arenediazonium ions: synthesis of 1,1-diacyl-2-arylhydrazines
  作者：Angelo Clerici、Ombretta Porta

  DOI：10.1021/jo00024a021

  日期：1991.11

  The alpha-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET). When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5). A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.