methyl (2S)-2-[(1R,11S,14S,17S,20S,23S)-14-methyl-11-[(2-methylpropan-2-yl)oxycarbonylamino]-17-(2-methylpropyl)-12,15,18,21-tetraoxo-2,13,16,19,22,24-hexazahexacyclo[18.10.1.12,9.01,23.03,8.025,30]dotriaconta-3,5,7,9(32),25,27,29-heptaen-22-yl]-3-phenylpropanoate | 1227608-45-8

• 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: methyl (2S)-2-[(1R,11S,14S,17S,20S,23S)-14-methyl-11-[(2-methylpropan-2-yl)oxycarbonylamino]-17-(2-methylpropyl)-12,15,18,21-tetraoxo-2,13,16,19,22,24-hexazahexacyclo[18.10.1.12,9.01,23.03,8.025,30]dotriaconta-3,5,7,9(32),25,27,29-heptaen-22-yl]-3-phenylpropanoate
• CAS: 1227608-45-8
• 化学式: C₄₆H₅₅N₇O₈
• 分子量: 833.985
• InChiKey: RWKXIQXVGCSYKG-IPCOSSDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  61
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  189
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(1R,11S,14S,17S,20S,23S)-14-methyl-11-[(2-methylpropan-2-yl)oxycarbonylamino]-17-(2-methylpropyl)-12,15,18,21-tetraoxo-2,13,16,19,22,24-hexazahexacyclo[18.10.1.12,9.01,23.03,8.025,30]dotriaconta-3,5,7,9(32),25,27,29-heptaen-22-yl]-3-phenylpropanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl (2S)-2-[(1R,11S,14S,17S,20S,23S)-14-methyl-11-[(2-methylpropan-2-yl)oxycarbonylamino]-17-(2-methylpropyl)-12,15,18,21-tetraoxo-2,13,16,19,22,24-hexazahexacyclo[18.10.1.12,9.01,23.03,8.025,30]dotriaconta-3,5,7,9(32),25,27,29-heptaen-22-yl]-3-phenylpropanoate 、
  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