N-(tert-butoxycarbonyl)-2-(1-hydroxy-2,3-butadien-2-yl)aniline | 958882-75-2

• 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: N-(tert-butoxycarbonyl)-2-(1-hydroxy-2,3-butadien-2-yl)aniline
• CAS: 958882-75-2
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: UQCSDBRDQWGTEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-2-(1-hydroxy-2,3-butadien-2-yl)aniline 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 9-tert-butyl (+/-)-(2R*,3R*)-2,3-dimethyl 1,2,3,4-tetrahydro-9H-carbazole-2,3,9-tricarboxylate
  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：

  N-(tert-butoxycarbonyl)-2-[1-(tert-butyldimethylsiloxy)-2,3-butadien-2-yl]aniline 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-(tert-butoxycarbonyl)-2-(1-hydroxy-2,3-butadien-2-yl)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

文献信息

• Generation of<i>N</i>-(<i>tert</i>-Butoxycarbonyl)indole-2,3-quinodimethane and Its [4+2]-Type Cycloaddition
  作者：Fuyuhiko Inagaki、Masaya Mizutani、Norikazu Kuroda、Chisato Mukai

  DOI：10.1021/jo901325d

  日期：2009.8.21

  The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K2CO3 or Pd2(dba)3 in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the

  通过使N-（叔丁氧基羰基）-2-（1-乙氧基羰氧基甲基甲基烯基）苯胺与K 2反应，开发了制备反应性N-（叔丁氧基羰基）吲哚-2,3-喹二甲烷中间体的两个条件。回流甲苯中的CO 3或Pd 2（dba）3。所得的N-（叔丁氧基羰基）吲哚-2,3-喹二甲烷被数个烯基和炔基二亲二烯体捕获，以提供相应的四氢-和二氢咔唑衍生物。