(E)-5-Acetoxy-2-methyl-pent-2-enoic acid methyl ester | 136823-43-3

• 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-Acetoxy-2-methyl-pent-2-enoic acid methyl ester
• CAS: 136823-43-3
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: IREQATAQMWJMKB-UHFFFAOYSA-N

物化性质

• 沸点：
  252.7±33.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 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：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  penta-3-yn-1-yl acetate 、 二氧化碳 、 碘甲烷 在 tris(2,2'-bipyridine)nickel(II) tetrafluoroborate 、 tetrabutylammonium tetrafluoroborate 、 potassium carbonate 、 magnesium 作用下， 生成 (E)-5-Acetoxy-2-methyl-pent-2-enoic acid methyl ester 、 (E)-2-(2-Acetoxy-ethyl)-but-2-enoic acid methyl ester
  参考文献：
  名称：

  From stoichiometry to catalysis: electroreductive coupling of alkynes and carbon dioxide with nickel-bipyridine complexes. Magnesium ions as the key for catalysis

  摘要：

  The incorporation of carbon dioxide into nonactivated alkynes catalyzed by electrogenerated nickel-bipyridine complexes affords alpha,beta-unsaturated acids in moderate to good yields. The electrocarboxylation reaction was undertaken on a preparative scale in the presence of a sacrificial magnesium anode: the formation of acids from alkynes is stoichiometric with respect to the nickel complex if performed in a two-compartment cell but can be made catalytic in a single-compartment cell. An intermediate nickelacycle was isolated from the reaction with 4-octyne. The cleavage of this metallacycle by magnesium ions is the key step to explain catalysis.

  DOI：

  10.1021/ja00022a037