Ethyl (E)-5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate | 133834-81-8

• 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: Ethyl (E)-5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate
• 英文别名: Ethyl (Z)-5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate；Ethyl 5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate
• CAS: 133834-81-8；133834-82-9
• 化学式: C₂₁H₂₀BrNO₃
• 分子量: 414.299
• InChiKey: GBFYVRDWBIJOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethyl (E)-5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到Ethyl 7-(benzyloxy)-9,9a-dihydro-3H-pyrrolo<1,2-a>indole-9a-carboxylate
  参考文献：
  名称：

  A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization

  摘要：

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.

  DOI：

  10.1021/jo00011a008
• 作为产物：
  描述：

  5-苄氧基吲哚-2-甲酸乙酯 、 1,3-dibromopropene 在 18-冠醚-6 、 potassium tert-butylate 作用下， 生成 Ethyl (E)-5-(benzyloxy)-1-(3-bromo-2-propenyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization

  摘要：

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.

  DOI：

  10.1021/jo00011a008

文献信息

• A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization
  作者：Frederick E. Ziegler、Lucio O. Jeroncic

  DOI：10.1021/jo00011a008

  日期：1991.5

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.