2-(1-acetoxy-2,3-butadien-2-yl)-N-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)aniline | 888732-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-acetoxy-2,3-butadien-2-yl)-N-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)aniline
• 英文别名: ethyl 3-(1-acetyloxybuta-2,3-dien-2-yl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate
• CAS: 888732-11-4
• 化学式: C₂₀H₂₅NO₆
• 分子量: 375.422
• InChiKey: UPDMBTHOWWRWPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(1-acetoxy-2,3-butadien-2-yl)-N-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)aniline 、 富马酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以69%的产率得到(2RS,3RS)-2,3-bis(methoxycarbonyl)-9-(tert-butoxycarbonyl)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  A Novel Generation of Indole-2,3-quinodimethanes

  摘要：

  A novel and efficient procedure for the generation of the reactive indole-2,3-quinodimethane intermediates from the allenylanilines is described. The indole-2,3-quinodimethane intermediates were captured by several dienophiles to afford the corresponding tetrahydro- and dihydrocarbazole derivatives. This method is significantly different from the previously reported ones, which involve the 1,4-elimination or its related reactions of the indole derivatives that possess suitable substituents at both the C-2 and C-3 positions.

  DOI：

  10.1021/ol060418n
• 作为产物：
  描述：

  4-tert-Butoxycarbonylamino-3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-propa-1,2-dienyl]-benzoic acid ethyl ester 在 吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(1-acetoxy-2,3-butadien-2-yl)-N-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)aniline
  参考文献：
  名称：

  A Novel Generation of Indole-2,3-quinodimethanes

  摘要：

  A novel and efficient procedure for the generation of the reactive indole-2,3-quinodimethane intermediates from the allenylanilines is described. The indole-2,3-quinodimethane intermediates were captured by several dienophiles to afford the corresponding tetrahydro- and dihydrocarbazole derivatives. This method is significantly different from the previously reported ones, which involve the 1,4-elimination or its related reactions of the indole derivatives that possess suitable substituents at both the C-2 and C-3 positions.

  DOI：

  10.1021/ol060418n