4-[1-(2-{3-bromo-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]-3-(indol-3-yl)-3-pyrroline-2,5-dione | 203719-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-[1-(2-{3-bromo-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]-3-(indol-3-yl)-3-pyrroline-2,5-dione
• 英文别名: 3-[1-[2-(4-bromo-1-trityloxybutan-2-yl)oxyethyl]indol-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 203719-75-9
• 化学式: C₄₅H₃₈BrN₃O₄
• 分子量: 764.718
• InChiKey: HAYMPGDUNLZCKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[1-(2-{3-bromo-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]-3-(indol-3-yl)-3-pyrroline-2,5-dione 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以73%的产率得到6,7,10,11-tetrahydro-9-[(triphenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione
  参考文献：
  名称：

  Cyclization Strategies for the Synthesis of Macrocyclic Bisindolylmaleimides

  摘要：

  Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl im ide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.

  DOI：

  10.1021/jo001605g
• 作为产物：
  描述：

  吲哚-3-乙醛酸甲酯 在 吡啶 、 亚磷酸三苯酯 、 potassium tert-butylate 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[1-(2-{3-bromo-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]-3-(indol-3-yl)-3-pyrroline-2,5-dione
  参考文献：
  名称：

  Cyclization Strategies for the Synthesis of Macrocyclic Bisindolylmaleimides

  摘要：

  Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl im ide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.

  DOI：

  10.1021/jo001605g

文献信息

• Cyclization Strategies for the Synthesis of Macrocyclic Bisindolylmaleimides
  作者：Margaret M. Faul、Christine A. Krumrich

  DOI：10.1021/jo001605g

  日期：2001.3.1

  Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl im ide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.