1-甲基-3-(o-叠氮苯基)-1H-喹啉-2-酮 | 251089-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-甲基-3-(o-叠氮苯基)-1H-喹啉-2-酮
• 英文名称: 1-methyl-3-(o-azidophenyl)-1H-quinoline-2-one
• 英文别名: 1-methyl-3-(o-azidophenyl)quinolin-2-one；3-(2-azidophenyl)-1-methylquinolin-2(1H)-one；1-Methyl-(o-azidophenyl)-quinoline-2-one；3-(2-azidophenyl)-1-methylquinolin-2-one
• CAS: 251089-12-0
• 化学式: C₁₆H₁₂N₄O
• 分子量: 276.297
• InChiKey: UNYKTKWHQXJXMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-3-(o-叠氮苯基)-1H-喹啉-2-酮 以 邻二甲苯 为溶剂， 反应 20.0h， 以82%的产率得到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 palladium on activated charcoal 盐酸 、 二苯并-18-冠醚-6 、 偶氮二异丁腈 、 硫酸 、 水 、 氢气 、 potassium carbonate 、 苯硫酚 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 硝基苯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 56.7h， 生成 1-甲基-3-(o-叠氮苯基)-1H-喹啉-2-酮
  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 direct synthesis of neocryptolepine and isocryptolepine
  作者：George A. Kraus、Haitao Guo

  DOI：10.1016/j.tetlet.2010.05.141

  日期：2010.8

  A formal synthesis of indolequinoline alkaloid neocryptolepine and isocryptolepine is described which employed a common intermediate and used an intramolecular Wittig reaction followed by regioselective methylation in excellent yield. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.

表征谱图