N-乙酰基-N'-(2,3-二氢-2-苯基-4H-1-苯并吡喃-4-亚基)乙酰肼 | 4924-22-5

• 物质功能分类: 有机原料 - 肼或胲的有机衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: N-乙酰基-N'-(2,3-二氢-2-苯基-4H-1-苯并吡喃-4-亚基)乙酰肼
• 英文名称: flavanone diacetylhydrazone
• 英文别名: Diacetyl-flavanon-hydrazon；2-phenyl-chroman-4-one diacetylhydrazone；N-acetyl-N'-(2,3-dihydro-2-phenyl-4H-1-benzopyran-4-ylidene)acetohydrazide；N-acetyl-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]acetamide
• CAS: 4924-22-5
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: UNGWSRDLOLQJGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基-N'-(2,3-二氢-2-苯基-4H-1-苯并吡喃-4-亚基)乙酰肼 、 乙酸酐 在 zinc(II) chloride 作用下， 反应 40.0h， 以67%的产率得到spiro<3-acetyl-5-methyl-2,3-dihydro-1,3,4-oxadiazole-2,4'-flavan>
  参考文献：
  名称：

  Reactions of flavonoid thiosemicarbazones under acetylating conditions

  摘要：

  Upon acetylation, (2-phenyl)dihydrobenzopyrone- and 2'-hydroxychalcone thiosemicarbazones (1c, 2c, 3c, and 7c) form 2,2-disubstituted 5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazoles (1i, 2i, 4i, and 8i) instead of the diacetylthiosemicarbazones (2e, 8e) claimed in the literature. Similarly, the reactions of the aromatic ketone thiosemicarbazones 9c, 10c and 11d result in the formation of thiadiazolines (9i, 10i, and 11k, respectively), flavone thiosemicarbazone (6c), however, is degraded to flavone diacetylhydrazone (6g) under the same conditions. The synthesis of the flavanone spiro-1,3,4-oxadiazoline 2h is also described.

  DOI：

  10.1016/s0040-4020(01)96219-2

文献信息

• Reactions of flavonoid thiosemicarbazones under acetylating conditions
  作者：László Somogyi

  DOI：10.1016/s0040-4020(01)96219-2

  日期：1991.11

  Upon acetylation, (2-phenyl)dihydrobenzopyrone- and 2'-hydroxychalcone thiosemicarbazones (1c, 2c, 3c, and 7c) form 2,2-disubstituted 5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazoles (1i, 2i, 4i, and 8i) instead of the diacetylthiosemicarbazones (2e, 8e) claimed in the literature. Similarly, the reactions of the aromatic ketone thiosemicarbazones 9c, 10c and 11d result in the formation of thiadiazolines (9i, 10i, and 11k, respectively), flavone thiosemicarbazone (6c), however, is degraded to flavone diacetylhydrazone (6g) under the same conditions. The synthesis of the flavanone spiro-1,3,4-oxadiazoline 2h is also described.