(6,6-Dimethyl-9-oxo-2,3,6,7,8,9-hexahydro-benzo[g]indol-1-yl)-acetic acid methyl ester | 887945-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6,6-Dimethyl-9-oxo-2,3,6,7,8,9-hexahydro-benzo[g]indol-1-yl)-acetic acid methyl ester
• CAS: 887945-84-8
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: ONKIFJJALMWHRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6,6-Dimethyl-9-oxo-2,3,6,7,8,9-hexahydro-benzo[g]indol-1-yl)-acetic acid methyl ester 在 sodium hydroxide 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 6,6-Dimethyl-1,4,5,6-tetrahydro-2H-2a-aza-cyclopenta[bc]acenaphthylene
  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：

  6,6-Dimethyl-9-oxo-2,3,5,5a,6,7,8,9-octahydro-benzo[g]indole-1-carboxylic acid tert-butyl ester 在 potassium carbonate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.5h， 生成 (6,6-Dimethyl-9-oxo-2,3,6,7,8,9-hexahydro-benzo[g]indol-1-yl)-acetic acid methyl 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