3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)indole | 925232-98-0

• 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-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)indole
• 英文别名: tert-butyl N-[[1-(methoxymethyl)indol-3-yl]methyl]-N-prop-2-enylcarbamate
• CAS: 925232-98-0
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: HGAYSRUSVIXJCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)indole 在 咪唑 、 叔丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 5.5h， 生成 3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-2-[1-(tert-butyldimethylsilyloxy)-2-propenyl]-1-(methoxymethyl)indole
  参考文献：
  名称：

  Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis

  摘要：

  The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by alpha-lithiation with subsequent electrophilic trapping with acrolein. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.043
• 作为产物：
  描述：

  1-(methoxymethyl)-1H-indole-3-carbaldehyde 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)indole
  参考文献：
  名称：

  Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis

  摘要：

  The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by alpha-lithiation with subsequent electrophilic trapping with acrolein. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.043

文献信息

• Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Daniel Solé、Sandra Alonso

  DOI：10.1016/j.tet.2006.11.043

  日期：2007.1

  The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by alpha-lithiation with subsequent electrophilic trapping with acrolein. (c) 2006 Elsevier Ltd. All rights reserved.