benzyl (2S,3aS,8bR)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-8b-[3-[(2S)-3-[[(2S)-1-[[(2S)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indol-1-yl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carboxylate | 1152312-14-5

• 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: benzyl (2S,3aS,8bR)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-8b-[3-[(2S)-3-[[(2S)-1-[[(2S)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indol-1-yl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carboxylate
• CAS: 1152312-14-5
• 化学式: C₆₁H₆₉N₇O₁₁
• 分子量: 1076.26
• InChiKey: ZDLAIAYZGFIRHS-PDLBTAODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  225
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3aS,8bR)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-8b-[3-[(2S)-3-[[(2S)-1-[[(2S)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indol-1-yl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  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：

  benzyl (2S)-4-methyl-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-triethylsilylpent-4-ynoyl]amino]propanoyl]amino]pentanoate 、 benzyl (2S,3aS,8bR)-8b-(2-iodoanilino)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carboxylate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到benzyl (2S,3aS,8bR)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-8b-[3-[(2S)-3-[[(2S)-1-[[(2S)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indol-1-yl]-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-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

文献信息

• Newhouse, Timothy; Lewis, Chad A.; Baran, Phil S., Journal of the American Chemical Society, 2009, vol. 131, p. 6360 - 6361
  作者：Newhouse, Timothy、Lewis, Chad A.、Baran, Phil S.

  DOI：——

  日期：——
• Scalable Total Syntheses of <i>N</i>-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F
  作者：Timothy Newhouse、Chad A. Lewis、Kyle J. Eastman、Phil S. Baran

  DOI：10.1021/ja1009458

  日期：2010.5.26

  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.