2-Hydroxy-4-methylene-hex-5-enoic acid methyl ester | 183562-29-0

• 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: 2-Hydroxy-4-methylene-hex-5-enoic acid methyl ester
• 英文别名: Methyl 2-hydroxy-4-methylidenehex-5-enoate；methyl 2-hydroxy-4-methylidenehex-5-enoate
• CAS: 183562-29-0
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: SPGYCJULHRZDCX-UHFFFAOYSA-N

物化性质

• 沸点：
  220.8±20.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛酸甲酯 、 天然橡胶 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate 、 2-Hydroxy-4-methylene-hex-5-enoic acid methyl 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

• A highly chemo- and enantio-selective hetero-Diels–Alder reaction catalysed by chiral aluminium complexes
  作者：Anette Graven、Mogens Johannsen、Karl Anker Jørgensen

  DOI：10.1039/cc9960002373

  日期：——

  A new, highly chemo- and enantio-selective catalytic hetero Diels-Alder reaction of conjugated dienes containing allylic C-H bonds with carbonyl compounds has been developed; with the use of (S)-(-)-BINOL-AlMe (BINOL = 1,1'-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels-Alder adduct as the major product with up to 97% ee.