methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate | 336883-73-9

• 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: methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate
• 英文别名: Methyl 2-[1-[3-(2-hydroxyethoxy)-4-phenylmethoxybutyl]indol-3-yl]-2-oxoacetate
• CAS: 336883-73-9
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: VLQRJLJGYBBUEF-UHFFFAOYSA-N

物化性质

• 沸点：
  608.2±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate 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， 反应 6.0h， 生成 3-{1-[3-(2-bromoethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-4-(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
• 作为产物：
  描述：

  4-indolylbutane-1,2-diol 在 锂硼氢 、 sodium hydride 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate
  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

• J. Org. Chem. 2001, 66, 2024-2033
  作者：

  DOI：——

  日期：——
• 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.