12-(benzotriazol-1-yl)-N,N-diethyl-12H-benzo[a]xanthen-9-amine | 197768-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 12-(benzotriazol-1-yl)-N,N-diethyl-12H-benzo[a]xanthen-9-amine
• CAS: 197768-81-3
• 化学式: C₂₇H₂₄N₄O
• 分子量: 420.514
• InChiKey: RJLZXXRYVXYHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴代十二烷 、 12-(benzotriazol-1-yl)-N,N-diethyl-12H-benzo[a]xanthen-9-amine 在 正丁基锂 、 高氯酸 作用下， 生成 (12-Dodecylbenzo[a]xanthen-9-ylidene)-diethylazanium;perchlorate
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of para-H-Substituted Pyrylium, Benzo[b]pyrylium, and Xanthylium Salts into para-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics)

  摘要：

  4H-Substituted pyrylium 9, benzo[b]pyrylium 15, and xanthylium salts 22 react with benzotriazole to give the corresponding 4H-(benzotriazol-l-yl)pyrans 10, benzo[b]pyrans 16, or xanthenes 23. Novel anion precursors 10, 16, and 23 undergo smooth lithiations at the positions a to the benzotriazol-1-yl function, i.e., at the para-position of the O-heterosycle. Subsequent trapping with different alkyl halides gives intermediates 14, 21, and 25, which are converted by mineral acid into para-functionalized pyrylium 11-13, benzo[b]pyrylium 17-20, and the xanthylium 24 salts in good to excellent yields.

  DOI：

  10.1021/jo971174a
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 在 tetrafluoroboric acid 、 sodium hydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.83h， 生成 12-(benzotriazol-1-yl)-N,N-diethyl-12H-benzo[a]xanthen-9-amine
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of para-H-Substituted Pyrylium, Benzo[b]pyrylium, and Xanthylium Salts into para-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics)

  摘要：

  4H-Substituted pyrylium 9, benzo[b]pyrylium 15, and xanthylium salts 22 react with benzotriazole to give the corresponding 4H-(benzotriazol-l-yl)pyrans 10, benzo[b]pyrans 16, or xanthenes 23. Novel anion precursors 10, 16, and 23 undergo smooth lithiations at the positions a to the benzotriazol-1-yl function, i.e., at the para-position of the O-heterosycle. Subsequent trapping with different alkyl halides gives intermediates 14, 21, and 25, which are converted by mineral acid into para-functionalized pyrylium 11-13, benzo[b]pyrylium 17-20, and the xanthylium 24 salts in good to excellent yields.

  DOI：

  10.1021/jo971174a

文献信息

• Benzotriazole-Mediated Conversions of <i>para</i>-H-Substituted Pyrylium, Benzo[<i>b</i>]pyrylium, and Xanthylium Salts into <i>para</i>-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics)
  作者：Alan R. Katritzky、Peter Czerney、Julian R. Levell

  DOI：10.1021/jo971174a

  日期：1997.11.1

  4H-Substituted pyrylium 9, benzo[b]pyrylium 15, and xanthylium salts 22 react with benzotriazole to give the corresponding 4H-(benzotriazol-l-yl)pyrans 10, benzo[b]pyrans 16, or xanthenes 23. Novel anion precursors 10, 16, and 23 undergo smooth lithiations at the positions a to the benzotriazol-1-yl function, i.e., at the para-position of the O-heterosycle. Subsequent trapping with different alkyl halides gives intermediates 14, 21, and 25, which are converted by mineral acid into para-functionalized pyrylium 11-13, benzo[b]pyrylium 17-20, and the xanthylium 24 salts in good to excellent yields.