2-(6-acetoxy-2-methylene-hept-4-ynyl)-2-methyl-malonic acid diethyl ester | 913977-14-7

• 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: 2-(6-acetoxy-2-methylene-hept-4-ynyl)-2-methyl-malonic acid diethyl ester
• 英文别名: Diethyl 2-(6-acetyloxy-2-methylidenehept-4-ynyl)-2-methylpropanedioate
• CAS: 913977-14-7
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: RDIYUDYDYRSLDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(6-acetoxy-2-methylene-hept-4-ynyl)-2-methyl-malonic acid diethyl ester 在 biphenylphosphine based Au(I) complex 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到2-(5-acetoxy-3-methyl-bicyclo[3.1.0]hex-3-en-1-ylmethyl)-2-methyl-malonic acid diethyl ester
  参考文献：
  名称：

  Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates:  An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-ones

  摘要：

  The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis.

  DOI：

  10.1021/ja064223m
• 作为产物：
  描述：

  6-(Chloromethyl)hept-6-en-3-yn-2-ol 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(6-acetoxy-2-methylene-hept-4-ynyl)-2-methyl-malonic acid diethyl ester
  参考文献：
  名称：

  Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates:  An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-ones

  摘要：

  The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis.

  DOI：

  10.1021/ja064223m

文献信息

• Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates:  An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-ones
  作者：Andrea Buzas、Fabien Gagosz

  DOI：10.1021/ja064223m

  日期：2006.10.1

  The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis.