(E)-Dimethyl(1,1-dimethylethyl)<<1-(1-methylethoxy)-1-propenyl>oxy>silane | 89043-56-1

• 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: (E)-Dimethyl(1,1-dimethylethyl)<<1-(1-methylethoxy)-1-propenyl>oxy>silane
• 英文别名: (Z)-Dimethyl(1,1-dimethylethyl)<<1-(1-methylethoxy)-1-propenyl>oxy>silane；1-<(tert-butyldimethylsilyl)oxy>-1-isopropoxyprop-1-ene；[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane；1-[(tert-butyldimethylsilyl)oxy]-1-isopropoxyprop-1-ene
• CAS: 89043-56-1；89043-57-2
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: UDIROIXGQIGECQ-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 0.5 Torr)
• 密度：
  0.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-Dimethyl(1,1-dimethylethyl)<<1-(1-methylethoxy)-1-propenyl>oxy>silane 、 苯甲醛 在 Fe(C₅H₅)(dppe)CO*PF₆ - acetone 作用下， 生成 propan-2-yl 3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  Cationic mono- and bi-nuclear iron complexes as Lewis acid catalysts in Mukaiyama reactions

  摘要：

  从单核和双核阳离子羰基铁络合物的光解中衍生出的有机金属路易斯酸是 Mukaiyama 醛醇反应的极佳催化剂。

  DOI：

  10.1039/c39920001634

文献信息

• Lewis Base Activation of Lewis Acids:  Catalytic, Enantioselective Addition of Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Gregory L. Beutner、Thomas Wynn、Martin D. Eastgate

  DOI：10.1021/ja047339w

  日期：2005.3.1

  The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can be activated by binding of a strongly Lewis basic chiral phosphoramide, leading to in situ formation of a chiral Lewis acid. This species has proven to be a competent

  路易斯酸的路易斯碱活化的概念已被简化用于催化甲硅烷基乙烯酮缩醛和甲硅烷基二烯醇醚与醛的羟醛反应。弱酸性物质四氯化硅 (SiCl4) 可以通过结合强路易斯碱性手性磷酰胺而被激活，导致手性路易斯酸的原位形成。该物质已被证明是将乙酸酯、丙酸酯和异丁酸酯衍生的甲硅烷基乙烯酮缩醛与共轭和非共轭醛进行羟醛加成反应的有效催化剂。此外，还证明了甲硅烷基二烯醇醚的乙烯基羟醛反应。高水平的区域-，抗非对映-，
• Acyclic stereoselection. 36. Simple diastereoselection in the Lewis acid mediated reactions of enol silanes with aldehydes
  作者：Clayton H. Heathcock、Steven K. Davidsen、Kathleen T. Hug、Lee A. Flippin

  DOI：10.1021/jo00365a033

  日期：1986.7
• Organolanthanide catalysis of a Mukaiyama addition reaction
  作者：Leyi Gong、Andrew Streitwieser

  DOI：10.1021/jo00313a002

  日期：1990.12

  Bis[bis(1,3-trimethylsilyl)cyclopentadienyl]-ytterbium(III) chloride, Cp''2YbCl, 2, is an effective catalyst in the presence of additional trimethylsilyl chloride for the reaction of silyl ester enolates, such as the trimethylsilyl enolate of methyl isobutyrate, 1, with aliphatic and aromatic aldehydes, to yield beta-silyloxy esters. The reaction shows good diastereoselection that is readily rationalized with a cyclic transition-state mechanism in which a key feature is the important role played by restricted coordination space around the lanthanide cation.