1-[2-(indol-3-yl)ethyl]-5-(N-{2-(indol-3-yl)ethyl}carbamoyl)piperidin-2-one | 853063-74-8

• 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: 1-[2-(indol-3-yl)ethyl]-5-(N-{2-(indol-3-yl)ethyl}carbamoyl)piperidin-2-one
• 英文别名: N,1-bis[2-(1H-indol-3-yl)ethyl]-6-oxopiperidine-3-carboxamide
• CAS: 853063-74-8
• 化学式: C₂₆H₂₈N₄O₂
• 分子量: 428.534
• InChiKey: LOQVEXYTNDTYSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-(indol-3-yl)ethyl]-5-(N-{2-(indol-3-yl)ethyl}carbamoyl)piperidin-2-one 在 4-二甲氨基吡啶 、 锂硼氢 、 sodium methylate 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.33h， 生成 1-[2-(1-tert-butoxylcarbonylindol-3-yl)ethyl]-5-hydroxymethylpiperidin-2-one
  参考文献：
  名称：

  Convenient Synthesis of Substituted Piperidinones from α,β-Unsaturated Amides:  Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine

  摘要：

  An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.

  DOI：

  10.1021/jo050261x
• 作为产物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)acrylamide 在 叔丁基二甲硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以90%的产率得到1-[2-(indol-3-yl)ethyl]-5-(N-{2-(indol-3-yl)ethyl}carbamoyl)piperidin-2-one
  参考文献：
  名称：

  Convenient Synthesis of Substituted Piperidinones from α,β-Unsaturated Amides:  Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine

  摘要：

  An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.

  DOI：

  10.1021/jo050261x

文献信息

• Convenient Synthesis of Substituted Piperidinones from α,β-Unsaturated Amides:  Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine
  作者：Kiyosei Takasu、Naoko Nishida、Akiko Tomimura、Masataka Ihara

  DOI：10.1021/jo050261x

  日期：2005.5.1

  An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.