Tert-butyl 5-(3,3-dimethyl-6-oxocyclohexen-1-yl)-4-ethenyl-2,3-dihydropyrrole-1-carboxylate | 887945-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: Tert-butyl 5-(3,3-dimethyl-6-oxocyclohexen-1-yl)-4-ethenyl-2,3-dihydropyrrole-1-carboxylate
• 英文别名: tert-butyl 5-(3,3-dimethyl-6-oxocyclohexen-1-yl)-4-ethenyl-2,3-dihydropyrrole-1-carboxylate
• CAS: 887945-81-5
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: VCSLKQPIZXQFOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 5-(3,3-dimethyl-6-oxocyclohexen-1-yl)-4-ethenyl-2,3-dihydropyrrole-1-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 6,6-dimethyl-9-oxo-2,3,6,7,8,9-hexahydrobenzo[g]indolecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Indoles via 6π-Electrocyclic Ring Closures of Trienecarbamates

  摘要：

  A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

  DOI：

  10.1021/ja060282o
• 作为产物：
  描述：

  4-vinyl-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester 、 2-碘-4,4-二甲基-2-环己烯-1-酮 在 正丁基锂 、 四甲基乙二胺 、 三甲基氯化锡 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.83h， 以158 mg的产率得到Tert-butyl 5-(3,3-dimethyl-6-oxocyclohexen-1-yl)-4-ethenyl-2,3-dihydropyrrole-1-carboxylate
  参考文献：
  名称：

  Synthesis of Indoles via 6π-Electrocyclic Ring Closures of Trienecarbamates

  摘要：

  A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

  DOI：

  10.1021/ja060282o

文献信息

• Synthesis of Indoles via 6π-Electrocyclic Ring Closures of Trienecarbamates
  作者：Thomas J. Greshock、Raymond L. Funk

  DOI：10.1021/ja060282o

  日期：2006.4.1

  A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.