N,N'-((5,5'-dimethoxy-1'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide | 1227608-14-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-((5,5'-dimethoxy-1'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide
• CAS: 1227608-14-1
• 化学式: C₂₆H₃₀N₄O₄
• 分子量: 462.549
• InChiKey: RKGITFJKANDRCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.38
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N'-((5,5'-dimethoxy-1'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到N,N'-((3'-chloro-5,5'-dimethoxy-3'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide
  参考文献：
  名称：

  Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F

  摘要：

  This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.

  DOI：

  10.1021/ja1009458
• 作为产物：
  描述：

  N,N'-((3'-hydroxy-5,5'-dimethoxy-3'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以96%的产率得到N,N'-((5,5'-dimethoxy-1'H-[1,2'-biindole]-3,3'-diyl)bis(ethane-2,1-diyl))diacetamide
  参考文献：
  名称：

  Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F

  摘要：

  This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.

  DOI：

  10.1021/ja1009458