2-[((E)-2-Isopropoxy-2-trimethylsilanyloxy-vinyloxy)-dimethyl-silanyl]-2-methyl-propane | 150811-61-3

• 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: 2-[((E)-2-Isopropoxy-2-trimethylsilanyloxy-vinyloxy)-dimethyl-silanyl]-2-methyl-propane
• 英文别名: tert-butyl-dimethyl-[(E)-2-propan-2-yloxy-2-trimethylsilyloxyethenoxy]silane
• CAS: 150811-61-3
• 化学式: C₁₄H₃₂O₃Si₂
• 分子量: 304.577
• InChiKey: ZBPZJKRRFPQEMY-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[((E)-2-Isopropoxy-2-trimethylsilanyloxy-vinyloxy)-dimethyl-silanyl]-2-methyl-propane 在 (R)-6,6'-dibromo-1,1'-bi-2-naphthol-1,2-dimethylimidazole-Zr(IV) 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(2-methoxy-phenylamino)-3-phenyl-propionic acid isopropyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Both Syn- and Anti-β-Amino Alcohols

  摘要：

  DOI：

  10.1021/ja973527t
• 作为产物：
  描述：

  isopropyl 2-((tert-butyldimethylsilyl)oxy)acetate 、 三甲基氯硅烷 生成 2-[((E)-2-Isopropoxy-2-trimethylsilanyloxy-vinyloxy)-dimethyl-silanyl]-2-methyl-propane
  参考文献：
  名称：

  Hattori Kouji, Yamamoto Hisashi, Tetrahedron, 50 (1994) N 10, S 3099-3112

  摘要：

  DOI：

文献信息

• Highly selective enolization method for heteroatom substituted esters; its application to the ireland ester enolate claisen rearrangement
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)81109-1

  日期：1994.3

  A method for the stereoselective synthesis of silyl ketene acetals from α-siloxy esters, β-hydroxy esters, and α-amino esters is described. Internal quench with excess trimethylsilyl chloride of the lithium enolate at −100 °C, which is generated using a hindered base, LTMP, leads to the selective formation of E-silyl ketene acetal. In contrast, the deprotonation at −100 °C using LHMDS in THF-HMPA (4:1)

  描述了一种由α-甲硅烷氧基酯，β-羟基酯和α-氨基酯立体选择性合成甲硅烷基烯酮缩醛的方法。使用受阻碱LTMP在-100°C下用过量的烯醇锂的三甲基甲硅烷基氯进行内部淬灭，可选择性地形成E-甲硅烷基乙烯酮缩醛。相反，使用LHMDS在THF-HMPA（4：1）中在-100°C进行去质子化，然后用叔丁基二甲基甲硅烷基氯进行处理，可以选择性地得到Z-甲硅烷基烯酮缩醛。该方法可用于爱尔兰酯烯酸酯克莱森重排的立体选择反应。
• Air-Stable, Storable, and Highly Selective Chiral Lewis Acid Catalyst
  作者：Masaharu Ueno、Haruro Ishitani、Shū Kobayashi

  DOI：10.1021/ol026452t

  日期：2002.10.1

  [GRAPHICS]An air-stable, storable, and highly selective chiral Lewis acid catalyst for asymmetric Mannich-type reactions has been developed, The catalyst can be stored for more than three months in air at room temperature without loss of activity, Moreover, it has also been demonstrated that the catalyst can be recovered and reused.
• Highly selective generation and application of (E)- and (Z)-silyl ketene acetals from .alpha.-hydroxy esters
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1021/jo00072a005

  日期：1993.9

  A method for the stereoselective synthesis of silyl ketene acetals from a-hydroxy esters is described. Internal quench with excess TMSCI of the lithium enolate at -100-degrees-C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal. In contrast, the deprotonation at -100-degrees-C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively. The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.