(+/-)-(1-methoxy-2,2,2-triphenylethyl)(phenyl)dimethylsilane | 952651-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (+/-)-(1-methoxy-2,2,2-triphenylethyl)(phenyl)dimethylsilane
• CAS: 952651-71-7
• 化学式: C₂₉H₃₀OSi
• 分子量: 422.642
• InChiKey: JZGZQLILTNAJAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1-methoxy-2,2,2-triphenylethyl)(phenyl)dimethylsilane 在 lithium aluminium tetrahydride 、 草酰氯 、 溴 、 铁粉 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.5h， 生成 (1'R)-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]acetaldehyde
  参考文献：
  名称：

  More than a Protective Group:  Synthesis and Applications of a New Chiral Silane

  摘要：

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

  DOI：

  10.1021/ol071382h
• 作为产物：
  描述：

  2,2,2-三苯基乙醛 、 苯基二甲基氯硅烷 、 硫酸二甲酯 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 以84%的产率得到(+/-)-(1-methoxy-2,2,2-triphenylethyl)(phenyl)dimethylsilane
  参考文献：
  名称：

  More than a Protective Group:  Synthesis and Applications of a New Chiral Silane

  摘要：

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

  DOI：

  10.1021/ol071382h