2-Hydroxy-3-(tetrahydro-furan-2-yl)-butyric acid methyl ester | 144694-09-7

• 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-3-(tetrahydro-furan-2-yl)-butyric acid methyl ester
• 英文别名: Methyl 2-hydroxy-3-(oxolan-2-yl)butanoate
• CAS: 144694-09-7
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: ATSSYSDGPLUUSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  乙醛酸甲酯 、 (4E)-[(4-hexenyl)oxy]triisopropylsilane 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 2-Hydroxy-3-(tetrahydro-furan-2-yl)-butyric acid methyl ester 、
  参考文献：
  名称：

  Remote asymmetric induction based on carbonyl-ene reactions with bishomoallylic silyl ethers: dramatic changeover of regioselectivity by the remarkable siloxy effect

  摘要：

  A new approach to remote asymmetric induction is described for not only a 1,4- but also a 1,5-relationship, which is based on the carbonyl-ene reactions with chiral bishomoallylic silyl ethers. Silyl ethers, rather than alkyl ethers, exhibit beta-regiospecificity. Remarkably high levels of remote asymmetric induction can then be established with chiral bishomoallylic ethers to provide eventually a simple and efficient method for asymmetric induction.

  DOI：

  10.1021/jo00049a011

文献信息

• Remote asymmetric induction based on carbonyl-ene reactions with bishomoallylic silyl ethers: dramatic changeover of regioselectivity by the remarkable siloxy effect
  作者：Masaki Shimizu、Koichi Mikami

  DOI：10.1021/jo00049a011

  日期：1992.11

  A new approach to remote asymmetric induction is described for not only a 1,4- but also a 1,5-relationship, which is based on the carbonyl-ene reactions with chiral bishomoallylic silyl ethers. Silyl ethers, rather than alkyl ethers, exhibit beta-regiospecificity. Remarkably high levels of remote asymmetric induction can then be established with chiral bishomoallylic ethers to provide eventually a simple and efficient method for asymmetric induction.