10-oxo-5,6,7,8,9,10-hexahydrobenzocyclooctenylcarbamic acid tert-butyl ester | 887945-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-oxo-5,6,7,8,9,10-hexahydrobenzocyclooctenylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(5-oxo-7,8,9,10-tetrahydro-6H-benzo[8]annulen-4-yl)carbamate
• CAS: 887945-44-0
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: DGQGVTKDFBOVBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  10-oxo-5,6,7,8,9,10-hexahydrobenzocyclooctenylcarbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以97%的产率得到4-amino-7,8,9,10-tetrahydro-6H-benzocycloocten-5-one
  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：

  (10-Oxo-4,4a,5,6,7,8,9,10-octahydro-benzocycloocten-1-yl)-carbamic 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 3.0h， 以93.9 mg的产率得到10-oxo-5,6,7,8,9,10-hexahydrobenzocyclooctenylcarbamic 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