dimethyl (E)-2-[(2-methyl-5-oxo-1-cyclopentenyl)-oxy]-2-butenedioate

• 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: dimethyl (E)-2-[(2-methyl-5-oxo-1-cyclopentenyl)-oxy]-2-butenedioate
• 英文别名: dimethyl (E)-2-(2-methyl-5-oxocyclopenten-1-yl)oxybut-2-enedioate
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: YNCVOEMNRQQYPI-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基环戊烯醇酮 、 丁炔二酸二甲酯 在 三丁基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以41%的产率得到dimethyl (E)-2-[(2-methyl-5-oxo-1-cyclopentenyl)-oxy]-2-butenedioate
  参考文献：
  名称：

  Tributylphosphine Catalyzed O -Vinylation of 2-Hydroxy-3-methyl-2-cyclopenten-1-one

  摘要：

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between tributylphosphine and dialkyl acetylenedicarboxylates by 2-hydroxy-3-methyl-2-cyclopenten-1-one leads to vinyltributylphosphonium salts, which undergo an addition-elimination reaction in CH2Cl2 at room temperature to produce dialkyl 2-[(2-methyl-5-oxo-1-cyclopentenyl)-oxy]-2-butenedioates (1:1 mixtures of E and Z isomers) in fairly high yields.

  DOI：

  10.1080/10426500307920

文献信息

• Tributylphosphine Catalyzed O -Vinylation of 2-Hydroxy-3-methyl-2-cyclopenten-1-one
  作者：Ali Ramazani、Bagher Mohammadi、Nader Noshiranzadeh

  DOI：10.1080/10426500307920

  日期：2003.3.1

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between tributylphosphine and dialkyl acetylenedicarboxylates by 2-hydroxy-3-methyl-2-cyclopenten-1-one leads to vinyltributylphosphonium salts, which undergo an addition-elimination reaction in CH2Cl2 at room temperature to produce dialkyl 2-[(2-methyl-5-oxo-1-cyclopentenyl)-oxy]-2-butenedioates (1:1 mixtures of E and Z isomers) in fairly high yields.