1-hydroxymethylpyrrolo[3,2-e]indole | 188730-30-5

• 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-hydroxymethylpyrrolo[3,2-e]indole
• 英文别名: 6H-pyrrolo[3,2-e]indol-3-ylmethanol
• CAS: 188730-30-5
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: XLBYBRNUBVDYHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hydroxymethylpyrrolo[3,2-e]indole 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到3,6-二氢吡咯并[3,2-e]吲哚
  参考文献：
  名称：

  Synthesis and reactivity of pyrrolo[3,2-e]indole: Removal of a N-BOM group from an unactivated indole

  摘要：

  A practical synthesis of pyrrolo[3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either 1-BOM-pyrrolo[3,2-e]indole (4, 42% from 5-nitroindole) or 1-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment bf the resulting 1-hydroxymethylpyrrolo[3,2-e]indole (5) with NaOH in THF afforded 1 (94% from 5). Limited studies on the chemistry of 1 are also presented. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00198-6
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-hydroxymethylpyrrolo[3,2-e]indole
  参考文献：
  名称：

  Synthesis and reactivity of pyrrolo[3,2-e]indole: Removal of a N-BOM group from an unactivated indole

  摘要：

  A practical synthesis of pyrrolo[3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either 1-BOM-pyrrolo[3,2-e]indole (4, 42% from 5-nitroindole) or 1-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment bf the resulting 1-hydroxymethylpyrrolo[3,2-e]indole (5) with NaOH in THF afforded 1 (94% from 5). Limited studies on the chemistry of 1 are also presented. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00198-6

文献信息

• Synthesis and reactivity of pyrrolo[3,2-e]indole: Removal of a N-BOM group from an unactivated indole
  作者：John E. Macor、James T. Forman、Ronald J. Post、Kevin Ryan

  DOI：10.1016/s0040-4039(97)00198-6

  日期：1997.3

  A practical synthesis of pyrrolo[3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either 1-BOM-pyrrolo[3,2-e]indole (4, 42% from 5-nitroindole) or 1-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment bf the resulting 1-hydroxymethylpyrrolo[3,2-e]indole (5) with NaOH in THF afforded 1 (94% from 5). Limited studies on the chemistry of 1 are also presented. (C) 1997 Elsevier Science Ltd.