3-[2,5-dihydro-4-(1H-imidazol-1-yl)-1-methyl-2,5-dioxo-1H-pyrrol-3-yl]-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester | 203850-95-7

• 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-[2,5-dihydro-4-(1H-imidazol-1-yl)-1-methyl-2,5-dioxo-1H-pyrrol-3-yl]-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester
• 英文别名: Tert-butyl 3-(4-imidazol-1-yl-1-methyl-2,5-dioxopyrrol-3-yl)indole-1-carboxylate
• CAS: 203850-95-7
• 化学式: C₂₁H₂₀N₄O₄
• 分子量: 392.414
• InChiKey: HBPGYYFMOXWXAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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-[2,5-dihydro-4-(1H-imidazol-1-yl)-1-methyl-2,5-dioxo-1H-pyrrol-3-yl]-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester 在 manganese(IV) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 5-Methyl-4,6-dioxo-5,6-dihydro-4H-2,3a,5,11-tetraaza-benzo[a]trindene-11-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
• 作为产物：
  描述：

  咪唑 、 tert-butyl 3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以60%的产率得到3-[2,5-dihydro-4-(1H-imidazol-1-yl)-1-methyl-2,5-dioxo-1H-pyrrol-3-yl]-1H-indole-1-carboxylic acid, 1,1-dimethylethyl 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.