(Z)-2-amino-2'-nitrostilbene | 251089-08-4

• 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: (Z)-2-amino-2'-nitrostilbene
• 英文别名: 2-[(Z)-2-(2-nitrophenyl)ethenyl]aniline
• CAS: 251089-08-4
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: DHRTUGBXYVGCKQ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-amino-2'-nitrostilbene 在 palladium on activated charcoal 偶氮二异丁腈 、 硫酸 、 氢气 、 potassium carbonate 、 苯硫酚 、 三乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 邻二甲苯 、 水 、 硝基苯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 35.7h， 生成 5-methyl-5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one
  参考文献：
  名称：

  A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes

  摘要：

  1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00597-x
• 作为产物：
  描述：

  (2-硝基苄基)三苯基溴化膦,一水化合物 在 盐酸 、 二苯并-18-冠醚-6 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (Z)-2-amino-2'-nitrostilbene
  参考文献：
  名称：

  A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes

  摘要：

  1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00597-x

文献信息

• A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids
  作者：Pilar M. Fresneda、Pedro Molina、S. Delgado

  DOI：10.1016/s0040-4039(99)01477-x

  日期：1999.10

  A seven-step synthesis of the 1-methyl-3-(o-azidophenyl)quinolin-2-one, a common intermediate for the synthesis of the cryptotackieine and cryptosanguinolentine alkaloids, is described. This intermediate is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes
  作者：Pilar M Fresneda、Pedro Molina、Santiago Delgado

  DOI：10.1016/s0040-4020(01)00597-x

  日期：2001.7

  1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2. (C) 2001 Elsevier Science Ltd. All rights reserved.