(1'R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]pent-3-en-2-one | 952651-76-2

• 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'R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]pent-3-en-2-one
• 英文别名: (E)-1-[[(1R)-1-methoxy-2,2,2-triphenylethyl]-dimethylsilyl]oxypent-3-en-2-one
• CAS: 952651-76-2
• 化学式: C₂₈H₃₂O₃Si
• 分子量: 444.646
• InChiKey: ZTTOBWVMQKTWON-BVOFGLOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]pent-3-en-2-one 、 环戊二烯 在 magnesium triflate 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以87%的产率得到(1'R,1S,2S,3R,4R)-1-(3-methylbicyclo[2.2.1]hept-5-en-2-yl)-2-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]ethanone
  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 在 lithium aluminium tetrahydride 、 草酰氯 、 邻苯二甲酸二甲酯 、 溴 、 lithium 、 铁粉 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 (1'R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]pent-3-en-2-one
  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

文献信息

• More than a Protective Group:  Synthesis and Applications of a New Chiral Silane
  作者：Maurizio Campagna、Michael Trzoss、Stefan Bienz

  DOI：10.1021/ol071382h

  日期：2007.9.1

  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.