ethyl 2-methyl-4-methylidene-5-oxo-tetrahydrofuran-2-carboxylate | 154492-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: ethyl 2-methyl-4-methylidene-5-oxo-tetrahydrofuran-2-carboxylate
• 英文别名: (+/-)-ethyl 2-methyl-4-methylene-tetrahydro-5-oxo-2-furancarboxylate；Ethyl 2-methyl-4-methylidene-5-oxooxolane-2-carboxylate
• CAS: 154492-32-7
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: SVWWRZKFWUJMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-4-methylidene-5-oxo-tetrahydrofuran-2-carboxylate 在 phosphate buffer 、 porcine pancreatic lipase 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (+)-ethyl 2-methyl-4-methylene-tetrahydro-5-oxo-2-furancarboxylate
  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：

  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

文献信息

• Fouquet, Eric; Gabriel, Andreas; Maillard, Bernard, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 590 - 598
  作者：Fouquet, Eric、Gabriel, Andreas、Maillard, Bernard、Pereyre, Michel

  DOI：——

  日期：——
• Reactivity of functionalized allyltrihalostannanes: An easy entry to α-methylene-γ-lactones
  作者：Eric Fouquet、Andreas Gabriel、Bernard Maillard、Michel Pereyre

  DOI：10.1016/s0040-4039(00)61555-1

  日期：1993.11

  Stable ester monoallyltin halides 2 are prepared in excellent yields and react easily with aldehydes and ketones under very mild conditions, to provide a usefull access to various alpha-methylene-gamma-lactones.