3-(2-Indol-1-yl-ethyl)-2-oxo-piperidine-3-carboxylic acid ethyl ester | 833436-57-0

• 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: 3-(2-Indol-1-yl-ethyl)-2-oxo-piperidine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-[2-(1H-indol-1-yl)ethyl]-2-oxopiperidine-3-carboxylate；ethyl 3-(2-indol-1-ylethyl)-2-oxopiperidine-3-carboxylate
• CAS: 833436-57-0
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: HQYGNJWNTHZEQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Indol-1-yl-ethyl)-2-oxo-piperidine-3-carboxylic acid ethyl ester 在 咪唑 、 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 3-(2-Indol-1-yl-ethyl)-2-oxo-piperidine-3-carboxylic acid (2-triisopropylsilanyloxy-ethyl)-amide
  参考文献：
  名称：

  Skeletal Diversity via a Folding Pathway:  Synthesis of Indole Alkaloid-Like Skeletons

  摘要：

  Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.

  DOI：

  10.1021/ol047945w
• 作为产物：
  描述：

  2-氧-3-哌啶羧酸乙酯 、 1-(2-iodoethyl)indole 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到3-(2-Indol-1-yl-ethyl)-2-oxo-piperidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Skeletal Diversity via a Folding Pathway:  Synthesis of Indole Alkaloid-Like Skeletons

  摘要：

  Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.

  DOI：

  10.1021/ol047945w

文献信息

• Skeletal Diversity via a Folding Pathway:  Synthesis of Indole Alkaloid-Like Skeletons
  作者：Hiroki Oguri、Stuart L. Schreiber

  DOI：10.1021/ol047945w

  日期：2005.1.1

  Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.