(3S)-(E)-1-(Dimethylphenylsilyl)-1-buten-3-yl hydroxyacetate | 146962-05-2

• 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: (3S)-(E)-1-(Dimethylphenylsilyl)-1-buten-3-yl hydroxyacetate
• 英文别名: [(E,2S)-4-[dimethyl(phenyl)silyl]but-3-en-2-yl] 2-hydroxyacetate
• CAS: 146962-05-2
• 化学式: C₁₄H₂₀O₃Si
• 分子量: 264.397
• InChiKey: MDZHFDKUFDLSOC-VMPCVLLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-(E)-1-(Dimethylphenylsilyl)-1-buten-3-yl hydroxyacetate 在 吡啶 、 正丁基锂 、 三甲基氯硅烷 、 氯化亚砜 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.08h， 生成 (2R,3R)-(E)-Methyl 3-(dimethylphenylsilyl)-2-hydroxyhex-4-enoate
  参考文献：
  名称：

  Sequential diastereoselective addition and palladium(II)-catalyzed allylic acetate transposition of syn- and anti-.alpha.-acetoxy-.beta.-silyl-(E)-hex-4-enoates with achiral acetals. Asymmetric synthesis of differentiated syn and anti 1,3-diol synthons

  摘要：

  syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.

  DOI：

  10.1021/jo00057a008
• 作为产物：
  描述：

  (3S)-1-(Dimethylphenylsilyl)-1-buten-3-ol 在 4-二甲氨基吡啶 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (3S)-(E)-1-(Dimethylphenylsilyl)-1-buten-3-yl hydroxyacetate
  参考文献：
  名称：

  Sequential diastereoselective addition and palladium(II)-catalyzed allylic acetate transposition of syn- and anti-.alpha.-acetoxy-.beta.-silyl-(E)-hex-4-enoates with achiral acetals. Asymmetric synthesis of differentiated syn and anti 1,3-diol synthons

  摘要：

  syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.

  DOI：

  10.1021/jo00057a008

文献信息

• Sequential diastereoselective addition and palladium(II)-catalyzed allylic acetate transposition of syn- and anti-.alpha.-acetoxy-.beta.-silyl-(E)-hex-4-enoates with achiral acetals. Asymmetric synthesis of differentiated syn and anti 1,3-diol synthons
  作者：James S. Panek、Michael Yang、Jason S. Solomon

  DOI：10.1021/jo00057a008

  日期：1993.2

  syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.