3-[N-(4-cyanophenyl)amino]-2-formylindole | 658041-40-8

• 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-[N-(4-cyanophenyl)amino]-2-formylindole
• 英文别名: 4-[(2-formyl-1H-indol-3-yl)amino]benzonitrile
• CAS: 658041-40-8
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: KYGXVOWOUJAJBT-UHFFFAOYSA-N

物化性质

• 熔点：
  243-244 °C(Solv: methanol (67-56-1))
• 沸点：
  529.4±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.68
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[N-(4-cyanophenyl)amino]-2-formylindole 在 palladium on activated charcoal 盐酸 、 盐酸羟胺 、 氢气 、 sodium acetate 、 sodium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 78.0h， 生成 1-(4-cyanophenyl)-2-oxo-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole
  参考文献：
  名称：

  摘要：

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.

  DOI：

  10.1023/a:1024887429776
• 作为产物：
  描述：

  对氨基苯腈 在 水 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 3-[N-(4-cyanophenyl)amino]-2-formylindole
  参考文献：
  名称：

  摘要：

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.

  DOI：

  10.1023/a:1024887429776

文献信息

• Synthesis of 4-aminopyrido[3,2-b]indole derivatives
  作者：S. Yu. Ryabova、L. M. Alekseeva、E. A. Lisitsa、V. G. Granik

  DOI：10.1007/s11172-006-0407-8

  日期：2006.7

  3-Arylamino-2-formylindoles were converted into oximes and then acetylated to give the corresponding O-acetyl derivatives. Chloroacetylation of the latter was accompanied by elimination of acetic acid, yielding 3-(N-aryl-N-chloroacetyl)amino-2-cyanoindoles. When heated in pyridine, these nitriles underwent cyclization into novel δ-carboline derivatives: 4-amino-1-aryl-2-oxo-1,2-dihydropyrido[3,2-b]indol-3-yl)pyridinium chlorides. The structures of the compounds obtained were proved by IR and 1H NMR spectroscopy and mass spectrometry.

  将 3-芳基氨基-2-甲酰基吲哚转化为肟，然后进行乙酰化，得到相应的 O-乙酰基衍生物。后者的氯乙酰化伴随着乙酸的消除，生成 3-（N-芳基-N-氯乙酰基）氨基-2-氰基吲哚。在吡啶中加热后，这些腈类发生环化反应，生成新型的 δ-咔啉衍生物：4-氨基-1-芳基-2-氧代-1,2-二氢吡啶并[3,2-b]吲哚-3-基）吡啶鎓氯化物。通过红外光谱、1H NMR 光谱和质谱分析证明了所获化合物的结构。