trimethyl((1-(methylthio)vinyl)oxy)silane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethyl((1-(methylthio)vinyl)oxy)silane
• 英文别名: Trimethyl(1-methylsulfanylethenoxy)silane；trimethyl(1-methylsulfanylethenoxy)silane
• 化学式: C₆H₁₄OSSi
• 分子量: 162.328
• InChiKey: ADLVGAGJVFGTIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxy-2,6-dimethylphenyl)pyrrolidine 、 trimethyl((1-(methylthio)vinyl)oxy)silane 在 三(五氟苯基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以52%的产率得到S-methyl 2-(1-(4-methoxy-2,6-dimethylphenyl)pyrrolidin-2-yl)ethanethioate
  参考文献：
  名称：

  B(C₆F₅)₃-Catalyzed C–H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant

  摘要：

  An efficient method for the coupling of N-alkylamines with silicon enolates to generate beta-amino carbonyl compounds is disclosed. These reactions proceed by activation of alpha-amino C-H bonds by B(C6F5)(3), which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.

  DOI：

  10.1021/acs.orglett.8b03959
• 作为产物：
  描述：

  三甲基氯硅烷 、 硫代乙酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 trimethyl((1-(methylthio)vinyl)oxy)silane
  参考文献：
  名称：

  B(C₆F₅)₃-Catalyzed C–H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant

  摘要：

  An efficient method for the coupling of N-alkylamines with silicon enolates to generate beta-amino carbonyl compounds is disclosed. These reactions proceed by activation of alpha-amino C-H bonds by B(C6F5)(3), which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.

  DOI：

  10.1021/acs.orglett.8b03959

文献信息

• B(C₆F₅)₃-Catalyzed C–H Alkylation of <i>N</i>-Alkylamines Using Silicon Enolates without External Oxidant
  作者：Jessica Z. Chan、Yejin Chang、Masayuki Wasa

  DOI：10.1021/acs.orglett.8b03959

  日期：2019.2.15

  An efficient method for the coupling of N-alkylamines with silicon enolates to generate beta-amino carbonyl compounds is disclosed. These reactions proceed by activation of alpha-amino C-H bonds by B(C6F5)(3), which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.