(9H-fluoren-9-yl)methyl (2S,3aR,8aS)-3a-((2-iodophenyl)amino)-2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate | 1227608-51-6

• 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: (9H-fluoren-9-yl)methyl (2S,3aR,8aS)-3a-((2-iodophenyl)amino)-2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate
• CAS: 1227608-51-6
• 化学式: C₄₂H₃₇IN₄O₅
• 分子量: 804.684
• InChiKey: OJSZDKDKBBDNMV-HWGCDURFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  52.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109.0
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (2S,3aR,8aS)-3a-((2-iodophenyl)amino)-2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate 在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到
  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：

  Fmoc-L-Trp-L-Phe-OCH₃ 、 2-碘苯胺 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以62%的产率得到(9H-fluoren-9-yl)methyl (2S,3aR,8aS)-3a-((2-iodophenyl)amino)-2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate
  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