9-tert-butyl 2-methyl 1,2,3,4-tetrahydro-9H-carbazole-2,9-dicarboxylate | 83020-30-8

• 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: 9-tert-butyl 2-methyl 1,2,3,4-tetrahydro-9H-carbazole-2,9-dicarboxylate
• 英文别名: 9-O-tert-butyl 2-O-methyl 1,2,3,4-tetrahydrocarbazole-2,9-dicarboxylate
• CAS: 83020-30-8
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: LISYVGRSKVZWSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-tert-butyl 2-methyl 1,2,3,4-tetrahydro-9H-carbazole-2,9-dicarboxylate 、 sodium methylate 、 甲醇 以61%的产率得到
  参考文献：
  名称：

  MARINELLI, E. R., TETRAHEDRON LETT., 1982, 23, N 27, 2745-2748

  摘要：

  DOI：
• 作为产物：
  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 2-methyl 1,2,3,4-tetrahydro-9H-carbazole-2,9-dicarboxylate
  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。
• A new method for the generation of indole-2,3-quinodimethanes and 2-(N-alkoxycarbonylamino)-1,3-dienes. Intramolecular Heck/Diels–Alder cycloaddition cascade starting from acyclic α-phosphono enecarbamates
  作者：Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1039/b704374k

  日期：——

  An intramolecular Heck/Diels–Alder cycloaddition cascade starting from acyclic α-phosphono enecarbamates has been developed to prepare nitrogen heterocycles viaindole-2,3-quinodimethanesand 2-(N-alkoxycarbonylamino)-1,3-dienes.

  一种从非环状α-膦基烯基氨基甲酸酯出发的分子内Heck/Diels–Alder环加成级联反应已被开发，用于通过吲哚-2,3-二甲烯和2-(N-烷氧羰基氨基)-1,3-二烯合成氮杂环。
• Generation and cycloaddition reactions of indole-2,3-quinodimethanes
  作者：Edmund R. Marinelli

  DOI：10.1016/s0040-4039(00)87447-x

  日期：——

  N-methyl and N-tert-butoxycarbonylindole-2,3-quinodimethanes ( and ) have been generated and observed to undergo intermolecular cycloaddition reactions with dienophiles.

  已经产生了N-甲基和N-叔丁氧基羰基吲哚-2，3-喹二甲烷（和），并观察到它们与亲双烯体进行了分子间的环加成反应。
• Indole-2,3-quinodimethanes: Generation, reactivity and regioselective control of intermolecular Diels-Alder reactions
  作者：Susan F. Vice、Helena Nandin de Carvalho、Nicholas G. Taylor、Gary I. Dmitrienko

  DOI：10.1016/s0040-4039(00)70679-4

  日期：1989.1

  N-acylindole-2,3-quinodimethanes generated at low temperature from the N-acyl-2,3-bis (bromomethyl)indoles undergo a variety of cycloadditions including the reversible chelotropic reaction with sulphur dioxide to yield the unreported 1,3-dihydrothieno[3,4-b]indole-2,2-dioxide 9. Successful attempts to control the regioselectivity of reactions with unsymmetrical dienophiles are described.

  N-酰基-2,3-双（溴甲基）吲哚在低温下生成的N-酰基吲哚-2,3-喹二甲烷经过多种环加成反应，包括与二氧化硫的可逆性变向反应，生成未报告的1,3-二氢噻吩并[3,4-b]吲哚-2,2-二氧化物9.描述了控制不对称亲二烯体反应的区域选择性的成功尝试。
• A Novel Generation of Indole-2,3-quinodimethanes
  作者：Norikazu Kuroda、Yukie Takahashi、Kazuo Yoshinaga、Chisato Mukai

  DOI：10.1021/ol060418n

  日期：2006.4.1

  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.