3-[1-Methyl-4-(3-methyl-3H-imidazol-4-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester | 203850-93-5

• 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: 3-[1-Methyl-4-(3-methyl-3H-imidazol-4-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3-[1-methyl-4-(3-methylimidazol-4-yl)-2,5-dioxopyrrol-3-yl]indole-1-carboxylate
• CAS: 203850-93-5
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: WJDGZEQLAQGOFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[1-Methyl-4-(3-methyl-3H-imidazol-4-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester 在 盐酸 、 氢氧化钾 、 ammonium acetate 作用下， 生成 didemnimide C
  参考文献：
  名称：

  Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer

  摘要：

  A key step in the synthesis of the marine alkaloid didemnimide C (Ic) is the Stille coupling between the urethane protected 3-bromo-4-(indol-3-yl)-1-methylmaleimide 3 and 5-tributylstannyl-1-methylimidazole (4). In this manner 1c can be obtained in four steps in 29% overall yield. Treatment of 3 with imidazolyl magnesium bromide affords the imidazol-1-yl compound 7 which can then be converted to the cycle derivatives 8 and 10 upon irradiation with a halogen lamp. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10410-0
• 作为产物：
  描述：

  tert-butyl 3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate 、 1-甲基-5-(三丁基锡基)咪唑 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以72%的产率得到3-[1-Methyl-4-(3-methyl-3H-imidazol-4-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer

  摘要：

  A key step in the synthesis of the marine alkaloid didemnimide C (Ic) is the Stille coupling between the urethane protected 3-bromo-4-(indol-3-yl)-1-methylmaleimide 3 and 5-tributylstannyl-1-methylimidazole (4). In this manner 1c can be obtained in four steps in 29% overall yield. Treatment of 3 with imidazolyl magnesium bromide affords the imidazol-1-yl compound 7 which can then be converted to the cycle derivatives 8 and 10 upon irradiation with a halogen lamp. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10410-0

文献信息

• Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer
  作者：Andreas Terpin、Christian Winklhofer、Susanne Schumann、Wolfgang Steglich

  DOI：10.1016/s0040-4020(97)10410-0

  日期：1998.2

  A key step in the synthesis of the marine alkaloid didemnimide C (Ic) is the Stille coupling between the urethane protected 3-bromo-4-(indol-3-yl)-1-methylmaleimide 3 and 5-tributylstannyl-1-methylimidazole (4). In this manner 1c can be obtained in four steps in 29% overall yield. Treatment of 3 with imidazolyl magnesium bromide affords the imidazol-1-yl compound 7 which can then be converted to the cycle derivatives 8 and 10 upon irradiation with a halogen lamp. (C) 1998 Elsevier Science Ltd. All rights reserved.