1-(6-oxocyclohex-1-enyl)buta-1,3-dienylcarbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-oxocyclohex-1-enyl)buta-1,3-dienylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1E)-1-(6-oxocyclohexen-1-yl)buta-1,3-dienyl]carbamate
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: KINNVYUJQGONJZ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-oxocyclohex-1-enyl)buta-1,3-dienylcarbamic acid tert-butyl ester 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 7.0h， 生成 tert-butyl N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate
  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：

  1-(tributylstannyl)buta-1,3-dienylcarbamic acid tert-butyl ester 、 1-(4-喹啉基)甲胺 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以81%的产率得到1-(6-oxocyclohex-1-enyl)buta-1,3-dienylcarbamic 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

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.