(E)-5-Methoxy-pent-2-enoic acid tert-butyl ester | 149311-01-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-Methoxy-pent-2-enoic acid tert-butyl ester
• CAS: 149311-01-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: PQJRIFLROOLJMB-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-5-Methoxy-pent-2-enoic acid tert-butyl ester 在 三氟乙酸 作用下， 以 苯 为溶剂， 以89%的产率得到(E)-5-Methoxypent-2-enoic acid
  参考文献：
  名称：

  A Diels-Alder approach to Stemona alkaloids: total synthesis of stenine

  摘要：

  A total synthesis of dl-stenine (4) is described. Key features involve (1) use of an intramolecular Diels-Alder cycloaddition-aminimide rearrangement sequence to construct the perhydroindole substructure (29 --> 36 --> 27), (2) application of an Eschenmoser-Claisen rearrangement-iodolactonization sequence to prepare the butenolide substructure (58 --> 59 --> 61), (3) use of a free-radical allylation to introduce the C(9)-ethyl group (61 --> 62), and (4) thermal cyclization of an amino ester to afford azepinone 68. A variety of intermolecular and intramolecular Diels-Alder reactions, including examples in which alpha,beta-unsaturated thioesters play the role of dienophile, are also described.

  DOI：

  10.1021/jo00067a015
• 作为产物：
  描述：

  3-甲氧基丙醛 、 alkaline earth salt of/the/ methylsulfuric acid 生成 tert-butyl (Z)-5-methoxypent-2-enoate 、 (E)-5-Methoxy-pent-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  A Diels-Alder approach to Stemona alkaloids: total synthesis of stenine

  摘要：

  A total synthesis of dl-stenine (4) is described. Key features involve (1) use of an intramolecular Diels-Alder cycloaddition-aminimide rearrangement sequence to construct the perhydroindole substructure (29 --> 36 --> 27), (2) application of an Eschenmoser-Claisen rearrangement-iodolactonization sequence to prepare the butenolide substructure (58 --> 59 --> 61), (3) use of a free-radical allylation to introduce the C(9)-ethyl group (61 --> 62), and (4) thermal cyclization of an amino ester to afford azepinone 68. A variety of intermolecular and intramolecular Diels-Alder reactions, including examples in which alpha,beta-unsaturated thioesters play the role of dienophile, are also described.

  DOI：

  10.1021/jo00067a015