methyl (2S,3R,5S)-5-decyl-2-hydroxy-2-methyloxolane-3-carboxylate | 126862-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: methyl (2S,3R,5S)-5-decyl-2-hydroxy-2-methyloxolane-3-carboxylate
• CAS: 126862-05-3
• 化学式: C₁₇H₃₂O₄
• 分子量: 300.439
• InChiKey: GGAMLSDWQZSQMO-ZOBUZTSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-十二烯十二碳烯α-十二碳烯α-十二碳烯 、 乙酰乙酸甲酯 在 氧气 、 cobalt(II) acetate 作用下， 以 溶剂黄146 为溶剂， 以70%的产率得到methyl (2S,3R,5S)-5-decyl-2-hydroxy-2-methyloxolane-3-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations

  摘要：

  Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.

  DOI：

  10.1016/s0040-4020(01)80924-8

文献信息

• Cobalt(II) acetate promoted addition of acetoacetate to terminal olefins: A highly stereoselective synthesis of 5-alkyl-2-hydroxy 2 methyl-3-methoxycarbonyl tetrahydrofurans
  作者：Javed Iqbal、T.K.Praveen Kumar、S. Manogaran

  DOI：10.1016/s0040-4039(01)80778-4

  日期：1989.1

  Methylacetoacetate and terminal olefins react in presence of Cobalt(II) acetate and Oxygen to give the titled compound(2) in a highly stereoselective manner and the structure of this compound is elucidated by 1H NMR simulation studies.

  乙酰乙酸甲酯和末端烯烃在乙酸钴（II）和氧气的存在下反应，以高度立体选择性的方式得到标题化合物（2），并且该化合物的结构通过1 H NMR模拟研究得以阐明。
• Stereoselective synthesis of substituted tetrahydrofurans - identification and analysis by proton NMR and MNDO, MM2 calculations
  作者：P. Tarakeshwar、Javed Iqbal、S. Manogaran

  DOI：10.1016/s0040-4020(01)80924-8

  日期：1991.1

  Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.