2-{1-[(triphenylmethoxy)methyl]but-3-enyloxy}ethan-1-ol | 336883-59-1

• 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: 2-{1-[(triphenylmethoxy)methyl]but-3-enyloxy}ethan-1-ol
• 英文别名: 2-(1-Trityloxypent-4-en-2-yloxy)ethanol
• CAS: 336883-59-1
• 化学式: C₂₆H₂₈O₃
• 分子量: 388.507
• InChiKey: ZPSZCZYUZXJZAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-{1-[(triphenylmethoxy)methyl]but-3-enyloxy}ethan-1-ol 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-[1-(2-{1-[(triphenylmethoxy)methyl]but-3-enyloxy}ethyl)indol-3-yl]ethanamide
  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：

  三苯甲氧基甲基环氧乙烷 在 六甲基磷酰三胺 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 2-{1-[(triphenylmethoxy)methyl]but-3-enyloxy}ethan-1-ol
  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.