(E)-[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane | 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)-[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane
• 英文别名: (E)-1-<(tert-butyldimethylsilyl)oxy>-1-isopropoxyprop-1-ene；(E)-Dimethyl(1,1-dimethylethyl)<<1-(1-methylethoxy)-1-propenyl>oxy>silane；(E)-tert-butyl((1-isopropoxyprop-1-en-1-yl)oxy)dimethylsilane；tert-butyl-dimethyl-[(E)-1-propan-2-yloxyprop-1-enoxy]silane
• CAS: 89043-56-1
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: UDIROIXGQIGECQ-PKNBQFBNSA-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
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane 在 N,N-diisopropylethylammonium perchlorate 作用下， 以 氘代氯仿 为溶剂， 生成 (Z)-[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane
  参考文献：
  名称：

  Thermodynamic results for geometrical isomerism in silyl ketene acetals

  摘要：

  DOI：

  10.1021/jo00182a031
• 作为产物：
  描述：

  丙酸异丙酯 、 叔丁基二甲基氯硅烷 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 (E)-[(1-isopropoxy)propenyloxy]-tert-butyldimethylsilane
  参考文献：
  名称：

  Acyclic stereoselection. 36. Simple diastereoselection in the Lewis acid mediated reactions of enol silanes with aldehydes

  摘要：

  DOI：

  10.1021/jo00365a033

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. 27. Simple diastereoselection in the lewis acid mediated reactions of enolsilanes with aldehydes.
  作者：Clayton H. Heathcock、Kathleen T. Hug、Lee A. Flippin

  DOI：10.1016/s0040-4039(01)81736-6

  日期：1984.1

  The Lewis acid mediated reactions of enolsilanes 1–11 with benzaldehyde and isobutyraldehyde have been investigated. With the exception of compound 4, essentially no stereoselectivity is observed.

  已经研究了路易斯酸介导的烯醇硅烷1-11与苯甲醛和异丁醛的反应。除了化合物4外，基本上没有观察到立体选择性。
• A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir
  作者：Manuel Peifer、Raphaëlle Berger、Valerie W. Shurtleff、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja502205q

  日期：2014.4.23

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
• Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes as Surfactant Molecules Which Enable Efficient Catalysis in ScCO₂
  作者：Ichiro Komoto、Shū Kobayashi

  DOI：10.1021/jo0353177

  日期：2004.2.1

  Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO(2), poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO(2). In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO(2). Formation of emulsions was observed in these reactions, and the systems were studied in detail.
• HEATHCOCK, C. H.;HUG, K. T.;FLIPPIN, L. A., TETRAHEDRON LETT., 1984, 25, N 52, 5973-5976
  作者：HEATHCOCK, C. H.、HUG, K. T.、FLIPPIN, L. A.

  DOI：——

  日期：——