2-(2-Isopropenyl-furan-3-yl)-3-vinyl-indole-1-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-Isopropenyl-furan-3-yl)-3-vinyl-indole-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3-ethenyl-2-(2-prop-1-en-2-ylfuran-3-yl)indole-1-carboxylate；tert-butyl 3-ethenyl-2-(2-prop-1-en-2-ylfuran-3-yl)indole-1-carboxylate
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: ZYWFWCRRWZXRCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-Isopropenyl-furan-3-yl)-3-vinyl-indole-1-carboxylic acid tert-butyl ester 反应 3.0h， 以82 mg的产率得到tert-butyl 2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]carbazole-6-carboxylate
  参考文献：
  名称：

  Metathesis Reactions for the Synthesis of Ring-Fused Carbazoles

  摘要：

  The metathesis reaction is used as a key step for the synthesis of the indolo [2,3-a]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1-carboxylate 25, presumably via a spontaneous pi(8) electrocyclization reaction.

  DOI：

  10.1021/jo051826s
• 作为产物：
  描述：

  2-(2-acetylfuran-3-yl)-1H-indole-3-carboxaldehyde 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.08h， 生成 2-(2-Isopropenyl-furan-3-yl)-3-vinyl-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Metathesis Reactions for the Synthesis of Ring-Fused Carbazoles

  摘要：

  The metathesis reaction is used as a key step for the synthesis of the indolo [2,3-a]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1-carboxylate 25, presumably via a spontaneous pi(8) electrocyclization reaction.

  DOI：

  10.1021/jo051826s

文献信息

• Metathesis Reactions for the Synthesis of Ring-Fused Carbazoles
  作者：Stephen C. Pelly、Christopher J. Parkinson、Willem A. L. van Otterlo、Charles B. de Koning

  DOI：10.1021/jo051826s

  日期：2005.12.1

  The metathesis reaction is used as a key step for the synthesis of the indolo [2,3-a]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1-carboxylate 25, presumably via a spontaneous pi(8) electrocyclization reaction.