tert-butyl (3S)-3-(acetyloxymethyl)-6-phenylmethoxy-5-[(1,1,1-trifluoro-4-methoxy-4-oxobut-2-en-2-yl)amino]-2,3-dihydroindole-1-carboxylate | 157904-25-1

• 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: tert-butyl (3S)-3-(acetyloxymethyl)-6-phenylmethoxy-5-[(1,1,1-trifluoro-4-methoxy-4-oxobut-2-en-2-yl)amino]-2,3-dihydroindole-1-carboxylate
• CAS: 157904-25-1
• 化学式: C₂₈H₃₁F₃N₂O₇
• 分子量: 564.559
• InChiKey: YAKAETNUGRAOCO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-(acetyloxymethyl)-6-phenylmethoxy-5-[(1,1,1-trifluoro-4-methoxy-4-oxobut-2-en-2-yl)amino]-2,3-dihydroindole-1-carboxylate 在 palladium diacetate 、 2,4-滴二甲胺盐 作用下， 反应 3.5h， 以58%的产率得到methyl (1S)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel cyclopropapyrroloindole(CPI) derivatives bearing methoxycarbonyl and trifluoromethyl groups

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminoester as a key step. Some of these novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives, dl-10c,d, (+)-10d, and (S)-21b were found to exhibit antitumor activity against murine leukemia and murine solid tumors more prominent than that of the known CPI derivatives dl-4 and the clinical trial candidates 5 and 7. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00288-6
• 作为产物：
  描述：

  4,4,4-三氟巴豆酸甲酯 、 (3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到tert-butyl (3S)-3-(acetyloxymethyl)-6-phenylmethoxy-5-[(1,1,1-trifluoro-4-methoxy-4-oxobut-2-en-2-yl)amino]-2,3-dihydroindole-1-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel cyclopropapyrroloindole(CPI) derivatives bearing methoxycarbonyl and trifluoromethyl groups

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminoester as a key step. Some of these novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives, dl-10c,d, (+)-10d, and (S)-21b were found to exhibit antitumor activity against murine leukemia and murine solid tumors more prominent than that of the known CPI derivatives dl-4 and the clinical trial candidates 5 and 7. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00288-6