E-4-ethoxycarbonylbut-3-enyl N-formyl-N-(5'-methoxypent-4'-enyl)glycinate | 1073517-78-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: E-4-ethoxycarbonylbut-3-enyl N-formyl-N-(5'-methoxypent-4'-enyl)glycinate
• 英文别名: ethyl (E)-5-[2-[formyl-[(E)-5-methoxypent-4-enyl]amino]acetyl]oxypent-2-enoate
• CAS: 1073517-78-8
• 化学式: C₁₆H₂₅NO₆
• 分子量: 327.378
• InChiKey: CIUDYAFROFCSLD-TWHYHQCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(5-methoxypent-4-enyl)formamine 、 ethyl (E)-5-(bromoacetoxy)pent-2-enoate 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 生成 4-ethoxycarbonylbut-3-enyl N-formyl-N-(5'-methoxypent-4'-enyl)glycinate 、 E-4-ethoxycarbonylbut-3-enyl N-formyl-N-(5'-methoxypent-4'-enyl)glycinate
  参考文献：
  名称：

  A Versatile Cascade of Intramolecular Vilsmeier−Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition toward Tricyclic Cores of Alkaloids

  摘要：

  In the pursuit of synthetic efficiency, we developed an innovative one-pot transformation of linear substrates into bi- and tricyclic adducts using a cascade of amide activation, nucleophilic cyclization, azomethine ylide generation, and subsequent inter- or intramolecular 1,3-dipolar cycloaddition. Despite the high density and variety of functional groups on the substrates, the sequence occurred with perfect chemoselectivity with good to excellent yields.

  DOI：

  10.1021/ol802010n

文献信息

• A Versatile Cascade of Intramolecular Vilsmeier−Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition toward Tricyclic Cores of Alkaloids
  作者：François Lévesque、Guillaume Bélanger

  DOI：10.1021/ol802010n

  日期：2008.11.6

  In the pursuit of synthetic efficiency, we developed an innovative one-pot transformation of linear substrates into bi- and tricyclic adducts using a cascade of amide activation, nucleophilic cyclization, azomethine ylide generation, and subsequent inter- or intramolecular 1,3-dipolar cycloaddition. Despite the high density and variety of functional groups on the substrates, the sequence occurred with perfect chemoselectivity with good to excellent yields.