tert-butyl 1-(indol-3-yl)-1,2,3,4-tetrahydrocarbazole-9-carboxylate | 1415566-70-9

• 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: tert-butyl 1-(indol-3-yl)-1,2,3,4-tetrahydrocarbazole-9-carboxylate
• 英文别名: tert-butyl 1-(1H-indol-3-yl)-1,2,3,4-tetrahydrocarbazole-9-carboxylate
• CAS: 1415566-70-9
• 化学式: C₂₅H₂₆N₂O₂
• 分子量: 386.494
• InChiKey: SZZWEOOPEDEXLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3,4-tetrahydrocarbazol-9-carboxylic acid tert-butyl ester 在 三氟甲磺酸三甲基硅酯 、 四丁基碘化铵 、 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 tert-butyl 1-(indol-3-yl)-1,2,3,4-tetrahydrocarbazole-9-carboxylate
  参考文献：
  名称：

  Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles

  摘要：

  A new method for direct alpha-functionalization of 2,3-disubstituted indoles has been developed. The present reaction provides alpha-acetoxy indole derivatives regioselectively under mild conditions using commercially available and nontoxic iodine reagents. This reaction is a useful synthetic tool because obtained alpha-acetoxy products can be transformed into various functionalized indoles by substitution reactions with nucleophiles.

  DOI：

  10.1021/ol302983t

文献信息

• Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles
  作者：Hisaaki Zaimoku、Takashi Hatta、Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol302983t

  日期：2012.12.7

  A new method for direct alpha-functionalization of 2,3-disubstituted indoles has been developed. The present reaction provides alpha-acetoxy indole derivatives regioselectively under mild conditions using commercially available and nontoxic iodine reagents. This reaction is a useful synthetic tool because obtained alpha-acetoxy products can be transformed into various functionalized indoles by substitution reactions with nucleophiles.