| 144694-07-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 144694-07-5
• 化学式: C₁₈H₃₆O₄Si
• 分子量: 344.567
• InChiKey: ZLUOYTMNQGAXRY-PMOIYJJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

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

• Prins cyclization to tetrahydrofuran units of polyether antibiotics: Remarkable siloxy effect for stereocontrolled cyclization
  作者：Koichi Mikami、Masaki Shimizu

  DOI：10.1016/s0040-4039(00)60962-0

  日期：1992.10

  A novel route to substituted tetrahydrofurans is described, which is based on the Lewis acid-promoted Prins cyclization with side chain formation of CC bond. Bishomoallylic silyl ethers, rather than the (chloro)benzyl ethers and esters, provide selectively tetrahydrofurans, indicating the siloxy effect for facilitating the cyclization.

  描述了一种新的取代四氢呋喃的方法，该方法基于路易斯酸促进的Prins环化反应，并形成侧链CC键。二烯丙基烯丙基甲硅烷基醚而不是（氯）苄基醚和酯提供选择性的四氢呋喃，表明甲硅烷氧基效应有助于环化。