(S,E)-N-(2-(1H-indol-3-yl)ethyl)-3-phenyl-N-(1-phenylethyl)prop-2-en-1-amine | 1446317-24-3

• 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: (S,E)-N-(2-(1H-indol-3-yl)ethyl)-3-phenyl-N-(1-phenylethyl)prop-2-en-1-amine
• 英文别名: (E)-N-[2-(1H-indol-3-yl)ethyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-en-1-amine
• CAS: 1446317-24-3
• 化学式: C₂₇H₂₈N₂
• 分子量: 380.533
• InChiKey: HVUNYRUDPPUZDE-FLSMSTFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Cinnamyl bromide 、 (S)-N-(2-(1H-indol-3-yl)ethyl)-1-phenylethanamine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以63%的产率得到(S,E)-N-(2-(1H-indol-3-yl)ethyl)-3-phenyl-N-(1-phenylethyl)prop-2-en-1-amine
  参考文献：
  名称：

  The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide

  摘要：

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.

  DOI：

  10.1055/s-0032-1316893

文献信息

• The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide
  作者：Leticia Quintero、Fernando Sartillo-Piscil、Lilia Fuentes、Mireya Hernández-Juarez、Joel Terán

  DOI：10.1055/s-0032-1316893

  日期：——

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.