5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-4-ylcarbamic acid tert-butyl ester | 887945-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-4-ylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(2-oxo-4-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)carbamate
• CAS: 887945-49-5
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: LLJUXYWYLYFZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-4-ylcarbamic acid tert-butyl ester 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(6,7-Dihydro-2-aza-dibenzo[cd,h]azulen-2-yl)-ethanone
  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：

  (5-Oxo-5,10,11,11a-tetrahydro-1H-dibenzo[a,d]cyclohepten-4-yl)-carbamic acid tert-butyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以151 mg的产率得到5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-4-ylcarbamic 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