1-Methyl-4-(2-oxocyclohexyl)indole-3-carbaldehyde | 866721-32-6

• 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: 1-Methyl-4-(2-oxocyclohexyl)indole-3-carbaldehyde
• CAS: 866721-32-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: VICRFANUTOIAAH-UHFFFAOYSA-N

物化性质

• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-4-(2-oxocyclohexyl)indole-3-carbaldehyde 在 三乙基硅烷 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到(2S,6R)-10-methyl-10-azatetracyclo[6.6.1.12,6.011,15]hexadeca-1(15),8,11,13-tetraen-16-one
  参考文献：
  名称：

  Rapid Access to the Welwitindolinone Alkaloid Skeleton by Cyclization of Indolecarboxaldehyde Substituted Cyclohexanones

  摘要：

  A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.

  DOI：

  10.1021/ol051239t
• 作为产物：
  描述：

  4-溴-1-甲基吲哚 在 palladium diacetate 、 potassium phosphate 、 2-(二环己基膦基)联苯 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 1-Methyl-4-(2-oxocyclohexyl)indole-3-carbaldehyde
  参考文献：
  名称：

  Rapid Access to the Welwitindolinone Alkaloid Skeleton by Cyclization of Indolecarboxaldehyde Substituted Cyclohexanones

  摘要：

  A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.

  DOI：

  10.1021/ol051239t

文献信息

• Rapid Access to the Welwitindolinone Alkaloid Skeleton by Cyclization of Indolecarboxaldehyde Substituted Cyclohexanones
  作者：Jérôme Baudoux、Alexander J. Blake、Nigel S. Simpkins

  DOI：10.1021/ol051239t

  日期：2005.9.1

  A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.