3-(2-nitrophenyl)quinolin-2(1H)-one | 251089-10-8

• 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
• 英文名称: 3-(2-nitrophenyl)quinolin-2(1H)-one
• 英文别名: 3-(2-nitrophenyl)-1H-quinolin-2-one
• CAS: 251089-10-8
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: AXOROIKMGHIIRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-nitrophenyl)quinolin-2(1H)-one 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙醇 、 邻二甲苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 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 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 硝基苯 为溶剂， 反应 42.2h， 生成 3-(2-nitrophenyl)quinolin-2(1H)-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

文献信息

• Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
  作者：María V. Méndez、Daniel A. Heredia、Enrique L. Larghi、Andrea B. J. Bracca、Teodoro S. Kaufman

  DOI：10.1039/c7ra05349e

  日期：——

  A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed

  据报道，从常见的中间体向吲哚喹啉新隐油菜碱和6-甲基喹啉有一种简便的方法。两种序列均旨在最大程度地利用可及的试剂和稳定的条件，因此既简单又有效。他们涉及用2-硝基苯基乙酸酰胺化2-氨基苯甲醛（通过铁介导的还原2-硝基苯甲醛制备），然后用K 2 CO 3辅助环化形成3-（2-硝基苯基）喹啉-2-一个作为共同的先驱。Me 2 CO 3介导的内酰胺的N-甲基化，硝基部分的还原和最终环化导致新隐油菜籽的总收率为55％，而环缩合和N-甲基化得到6-甲基喹啉的总产率为79％。因此，朝向靶标的序列需要进行两次POCl 3促进的C–N键形成反应，两次Fe介导的硝基还原和两次碱基促进的转化。
• Metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones
  作者：Alexander V. Aksenov、Alexander N. Smirnov、Nicolai A. Aksenov、Inna V. Aksenova、Jonathon P. Matheny、Michael Rubin

  DOI：10.1039/c4ra14406f

  日期：——

  3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation

  3-取代的2-喹诺酮是通过2-硝基烯烃与2-取代的吲哚在多磷酸中的新型无金属环转移反应获得的。这种酸介导的级联转化通过ANRORC（亲核试剂的添加，开环和闭环）机理进行操作，可以与Fisher吲哚合成结合使用，以提供一种实用的三组分杂环化方法从芳基肼，2-硝基烯烃和苯乙酮。还证明了该化学方法的另一种选择，该方法采用了富电子芳烃和戊烯与1-（2-吲哚基）-2-硝基烯烃的烷基化反应。
• 666. Internuclear cyclisation. Part II. The application of the Pschorr reaction to some substituted derivatives of o-amino-α-phenylcinnamic acid
  作者：D. H. Hey、John M. Osbond

  DOI：10.1039/jr9490003172

  日期：——
• 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.