spiro<5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazole-2,4'-trans-3'-acetoxyflavan> | 139061-55-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: spiro<5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazole-2,4'-trans-3'-acetoxyflavan>
• 英文别名: spiro[5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazole-2,4'-trans-3'-acetoxyflavan]；[(2'R,3'R)-5-acetamido-3-acetyl-2'-phenylspiro[1,3,4-thiadiazole-2,4'-2,3-dihydrochromene]-3'-yl] acetate
• CAS: 139061-55-5；139164-36-6
• 化学式: C₂₂H₂₁N₃O₅S
• 分子量: 439.492
• InChiKey: AOSXKULFUSDLKS-JLMWTWJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97.3
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 spiro<5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazole-2,4'-trans-3'-acetoxyflavan>
  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