4-ethoxycarbonyl-4-hydroxy-2-methylidenepentanoic acid | 389063-31-4

• 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: 4-ethoxycarbonyl-4-hydroxy-2-methylidenepentanoic acid
• 英文别名: 2-(2-ethoxycarbonyl-2-hydroxypropyl)acrylic acid；5-Ethoxy-4-hydroxy-4-methyl-2-methylidene-5-oxopentanoic acid
• CAS: 389063-31-4
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: XLILKSFNPXFFEM-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±42.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonyl-4-hydroxy-2-methylidenepentanoic acid 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 ethyl 2-methyl-4-methylidene-5-oxo-tetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Enzymic resolution of an α-methylene-γ-lactonic ester

  摘要：

  The possibility of using enzymes for the kinetic resolution of an alpha-methylene-gamma-lactone was explored. The probe molecule, ethyl 2-methyl-4-methylene-tetrahydro-5-oxo-2-furancarboxylate was successfully resolved with Porcine pancreatic lipase and Candida rugosa lipase, in the presence of a cosolvent, leading to both enantiomers of the corresponding acid with high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00309-8
• 作为产物：
  描述：

  丙酮酸乙酯 、 2-(溴甲基)丙烯酸 在 indium 作用下， 以 水 为溶剂， 以67%的产率得到4-ethoxycarbonyl-4-hydroxy-2-methylidenepentanoic acid
  参考文献：
  名称：

  α-酮酯与烯丙基卤的介导烯丙基化*

  摘要：

  α-酮酯与烯丙基卤化物、炔丙基溴化物和烯丙基溴化物使用铟金属的化学选择性反应在温和条件下以良好至极好的产率提供了 α-羟基-γ,δ-不饱和酯。*本文献给李昌焕教授 60 岁生日。

  DOI：

  10.1081/scc-100105896

文献信息

• Enzymic resolution of an α-methylene-γ-lactonic ester
  作者：Giuliana Pitacco、Andrea Sessanta o Santi、Ennio Valentin

  DOI：10.1016/s0957-4166(00)00309-8

  日期：2000.8

  The possibility of using enzymes for the kinetic resolution of an alpha-methylene-gamma-lactone was explored. The probe molecule, ethyl 2-methyl-4-methylene-tetrahydro-5-oxo-2-furancarboxylate was successfully resolved with Porcine pancreatic lipase and Candida rugosa lipase, in the presence of a cosolvent, leading to both enantiomers of the corresponding acid with high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.
• In-MEDIATED ALLYLATION OF α-KETO ESTERS WITH ALLYL HALIDES^*
  作者：Phil Ho Lee、Kooyeon Lee、Sukbok Chang

  DOI：10.1081/scc-100105896

  日期：2001.1

  The chemoselective reaction of α-keto esters with allyl halides, propargyl bromides, and allenyl bromide using indium metal afforded α-hydroxy-γ,δ-unsaturated esters in good to excellent yields under mild conditions. *This paper is dedicated to Professor Chang Hwan Rhee on the occasion of his 60th birthday.

  α-酮酯与烯丙基卤化物、炔丙基溴化物和烯丙基溴化物使用铟金属的化学选择性反应在温和条件下以良好至极好的产率提供了 α-羟基-γ,δ-不饱和酯。*本文献给李昌焕教授 60 岁生日。