ethyl (Z)-5-[2-(1H-indol-3-yl)ethylamino]-3-oxopent-4-enoate | 83925-57-9

• 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: ethyl (Z)-5-[2-(1H-indol-3-yl)ethylamino]-3-oxopent-4-enoate
• CAS: 83925-57-9
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: UDRUXCUTMIDESO-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-5-[2-(1H-indol-3-yl)ethylamino]-3-oxopent-4-enoate 在 盐酸 、 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolidine-2,4-dione
  参考文献：
  名称：

  Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines

  摘要：

  Unprecedented 1,2,3-trisubstituted tetrahydro-beta-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring-closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00751-6
• 作为产物：
  描述：

  色胺 、 Ethyl 3-oxo-4-(3,4,4-trimethyl-1,3-oxazolidin-2-yl)butanoate 以 溶剂黄146 、 乙腈 为溶剂， 生成 ethyl (Z)-5-[2-(1H-indol-3-yl)ethylamino]-3-oxopent-4-enoate
  参考文献：
  名称：

  Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines

  摘要：

  Unprecedented 1,2,3-trisubstituted tetrahydro-beta-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring-closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00751-6

文献信息

• Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines
  作者：Kamaljit Singh、Prasant K Deb

  DOI：10.1016/s0040-4039(00)00751-6

  日期：2000.6

  Unprecedented 1,2,3-trisubstituted tetrahydro-beta-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring-closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.