3-cyano-2-p-nitrophenyl(phenyl)amino-5H-pyrido[3,2-b]indole | 355021-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-cyano-2-p-nitrophenyl(phenyl)amino-5H-pyrido[3,2-b]indole
• 英文别名: 2-[(4-nitrophenyl)phenylamino]-5H-pyrido-[3,2-b]indole-3-carbonitrile；2-[(4-nitrophenyl)(phenyl)amino]-5H-pyrido[3,2-b]indole-3-carbonitrile；2-(N-(4-nitrophenyl)anilino)-5H-pyrido[3,2-b]indole-3-carbonitrile
• CAS: 355021-78-2
• 化学式: C₂₄H₁₅N₅O₂
• mdl: MFCD03828158
• 分子量: 405.415
• InChiKey: INETVEGDAVNDPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyano-2-p-nitrophenyl(phenyl)amino-5H-pyrido[3,2-b]indole 、 碘甲烷 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到3-cyano-5-methyl-2-p-nitrophenyl(phenyl)amino-5H-pyrido[3,2-b]indole
  参考文献：
  名称：

  摘要：

  The possibility of transformation of 3-cyano-1-p-nitrophenyl-delta-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyanol-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (delta-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-delta-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3.2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.

  DOI：

  10.1023/a:1012749426699
• 作为产物：
  描述：

  3-cyano-1-p-nitrophenyl-2-phenylimino-1,2-dihydro-5H-pyrido[3,2-b]indole 以70%的产率得到3-cyano-2-p-nitrophenyl(phenyl)amino-5H-pyrido[3,2-b]indole
  参考文献：
  名称：

  摘要：

  The possibility of transformation of 3-cyano-1-p-nitrophenyl-delta-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyanol-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (delta-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-delta-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3.2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.

  DOI：

  10.1023/a:1012749426699

文献信息

• ——
  作者：S. Yu. Ryabova、L. M. Alekseeva、E. A. Lisitza、A. S. Shashkov、V. V. Chernyshev、G. B. Tichomirova、M. S. Goyzman、V. G. Granik

  DOI：10.1023/a:1012749426699

  日期：——

  The possibility of transformation of 3-cyano-1-p-nitrophenyl-delta-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyanol-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (delta-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-delta-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3.2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.