5-Hexenoic acid, 2-hydroxy-4-methylene-, butyl ester | 19353-24-3

• 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: 5-Hexenoic acid, 2-hydroxy-4-methylene-, butyl ester
• 英文别名: butyl 2-hydroxy-4-methylidenehex-5-enoate
• CAS: 19353-24-3
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: AXWITYBCCBRQFC-UHFFFAOYSA-N

物化性质

• 沸点：
  276.3±20.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Hexenoic acid, 2-hydroxy-4-methylene-, butyl ester 在 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Aqueous hetero Diels-Alder reactions: The carbonyl case.

  摘要：

  Commercially available aqueous solution of glyoxylic acid, pyruvaldehyde and glyoxal were shown to react with cyclic or non-cyclic dienes to give the corresponding cycloadducts and/or alpha-hydroxy gamma-lactones. Activated ketone (Pyruvic acid) was shown to react as well in the same conditions.

  DOI：

  10.1016/s0040-4020(01)81759-2
• 作为产物：
  描述：

  乙醛酸正丁酯 、 天然橡胶 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 生成 butyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate 、 5-Hexenoic acid, 2-hydroxy-4-methylene-, butyl ester
  参考文献：
  名称：

  Glyoxylate-Ene Reaction Catalyzed by Ln(OTf)3

  摘要：

  Yb(OTf)(3), can catalyze the glyoxylate-ene reaction effectively as a water-stable and reusable catalyst. Moreover, the selectivity of DA product or ene product can be adjusted by solvents in the reaction of glyoxylates with a diene (isoprene). In the presence of chiral ytterbium complexes generated in situ from Yb(OTf)(3) and optical 6,6'-disubstituted binaphthols, methyl glyoxylate smoothly reacts with alpha-methyl styrene to afford alpha-hydroxyl esters in modest optical yields. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01536-0

文献信息

• Glyoxylate-Ene Reaction Catalyzed by Ln(OTf)3
  作者：Changtao Qian、Taisheng Huang

  DOI：10.1016/s0040-4039(97)01536-0

  日期：1997.9

  Yb(OTf)(3), can catalyze the glyoxylate-ene reaction effectively as a water-stable and reusable catalyst. Moreover, the selectivity of DA product or ene product can be adjusted by solvents in the reaction of glyoxylates with a diene (isoprene). In the presence of chiral ytterbium complexes generated in situ from Yb(OTf)(3) and optical 6,6'-disubstituted binaphthols, methyl glyoxylate smoothly reacts with alpha-methyl styrene to afford alpha-hydroxyl esters in modest optical yields. (C) 1997 Elsevier Science Ltd.
• Aqueous hetero Diels-Alder reactions: The carbonyl case.
  作者：A. Lubineau、J. Augé、E. Grand、N. Lubin

  DOI：10.1016/s0040-4020(01)81759-2

  日期：1994.8

  Commercially available aqueous solution of glyoxylic acid, pyruvaldehyde and glyoxal were shown to react with cyclic or non-cyclic dienes to give the corresponding cycloadducts and/or alpha-hydroxy gamma-lactones. Activated ketone (Pyruvic acid) was shown to react as well in the same conditions.