3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)-2-propenoylindole | 925233-01-8

• 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-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)-2-propenoylindole
• 英文别名: tert-butyl N-[[1-(methoxymethyl)-2-prop-2-enoylindol-3-yl]methyl]-N-prop-2-enylcarbamate
• CAS: 925233-01-8
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: LVCZRGYZKWQKQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)-2-propenoylindole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-(tert-butoxycarbonyl)-7-(methoxymethyl)-6-oxo-1,2,3,6-tetrahydroazocino[4,3-b]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 manganese(IV) oxide 、 叔丁基锂 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 69.5h， 生成 3-[(N-allyl-N-tert-butoxycarbonyl)aminomethyl]-1-(methoxymethyl)-2-propenoylindole
  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.