N-Cinnamyl-3-oxopyrano<4,3-b>indole-1-carboxamide | 138956-02-2

• 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: N-Cinnamyl-3-oxopyrano<4,3-b>indole-1-carboxamide
• CAS: 138956-02-2
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: MHSBDMFGXJHVRA-UHFFFAOYSA-N

物化性质

• 沸点：
  629.5±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75.1
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-Cinnamyl-3-oxopyrano<4,3-b>indole-1-carboxamide 以 various solvent(s) 为溶剂， 反应 80.0h， 以43%的产率得到4-Phenyl-2,3-dihydro-2H,6H-pyrrolo<3,4-c>carbazol-1-one
  参考文献：
  名称：

  Synthesis of the staurosporine aglycon

  摘要：

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.

  DOI：

  10.1021/jo00033a036
• 作为产物：
  描述：

  肉桂基氯 在 potassium iodide 氢氧化钾 、 乙酸酐 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.5h， 生成 N-Cinnamyl-3-oxopyrano<4,3-b>indole-1-carboxamide
  参考文献：
  名称：

  Synthesis of the staurosporine aglycon

  摘要：

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.

  DOI：

  10.1021/jo00033a036

文献信息

• Synthesis of the staurosporine aglycon
  作者：Christopher J. Moody、Kulsum F. Rahimtoola、Barry Porter、Barry C. Ross

  DOI：10.1021/jo00033a036

  日期：1992.3

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.