methyl 3-[tert-butyl(diphenyl)silyl]oxy-4-methyl-2-methylidenepentanoate | 166763-11-7

• 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: methyl 3-[tert-butyl(diphenyl)silyl]oxy-4-methyl-2-methylidenepentanoate
• CAS: 166763-11-7
• 化学式: C₂₄H₃₂O₃Si
• 分子量: 396.602
• InChiKey: CTHFHWMPTJYNNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[tert-butyl(diphenyl)silyl]oxy-4-methyl-2-methylidenepentanoate 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  13-Asymmetric induction in the aldol reactions of α-methylene-β-alkoxy aldehydes

  摘要：

  The aldol reactions of the alpha-methylene-beta-alkoxy aldehydes 3 and 6 were examined for a range of Ti(IV), Sn(II), and B enolates. The sense and level of 1,3-asymmetric induction (up to 95% ds) varies with the enolate structure and the beta-hydroxyl protecting group in the aldehyde.

  DOI：

  10.1016/s0040-4039(00)79361-0
• 作为产物：
  描述：

  methyl 3-hydroxy-4-methyl-2-methylenepentanoate 、 叔丁基二苯基氯硅烷 在 咪唑 、 比沙可啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 3-[tert-butyl(diphenyl)silyl]oxy-4-methyl-2-methylidenepentanoate
  参考文献：
  名称：

  13-Asymmetric induction in the aldol reactions of α-methylene-β-alkoxy aldehydes

  摘要：

  The aldol reactions of the alpha-methylene-beta-alkoxy aldehydes 3 and 6 were examined for a range of Ti(IV), Sn(II), and B enolates. The sense and level of 1,3-asymmetric induction (up to 95% ds) varies with the enolate structure and the beta-hydroxyl protecting group in the aldehyde.

  DOI：

  10.1016/s0040-4039(00)79361-0

文献信息

• Acyclic Stereocontrol of Free Radical Reactions Involving Alkyl 2-(1-Hydroxyalkyl)propenoates
  作者：FW Eastwood、RD Mifsud、P Perlmutter

  DOI：10.1071/ch9942187

  日期：——

  The addition of cyclohexyl and t-butyl free radicals to silylated derivatives of alkyl 2-(1-hydroxyalkyl) propenoates was found to be stereoselective . In the case of the cyclohexyl radical the stereoselectivity was dependent upon the conditions used to generate the free radical and to quench the intermediate. Stereoselectivity in additions of the t-butyl radical was found to be temperature-dependent. In all cases stereoselectivity increased as the steric bulk of the group attached to the carbinol oxygen increased. A simple model which accounts for the stereoselectivity is proposed.

  研究发现，环己基和叔丁基自由基与 2-（1-羟基烷基）丙烯酸烷基硅烷化衍生物的加成具有立体选择性。环己基自由基的立体选择性取决于生成自由基和淬灭中间体的条件。研究发现，t-丁基自由基加成的立体选择性与温度有关。在所有情况下，立体选择性都会随着连接到羰基氧上的基团立体体积的增加而增加。提出了一个解释立体选择性的简单模型。
• Eastwood Frank W., Mifsud Roger D., Perlmutter Patrick, Austral. J. Chem., 47 (1994) N 12, S 2187-2200
  作者：Eastwood Frank W., Mifsud Roger D., Perlmutter Patrick

  DOI：——

  日期：——