{[(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enyl]-dimethyl-silanyl}-benzene | 889654-25-5

• 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: {[(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enyl]-dimethyl-silanyl}-benzene
• 英文别名: tert-butyl-[(Z)-1-[dimethyl(phenyl)silyl]-2-methylbut-2-enoxy]-dimethylsilane
• CAS: 889654-25-5
• 化学式: C₁₉H₃₄OSi₂
• 分子量: 334.649
• InChiKey: SWBUBVADQGESAH-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  {[(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enyl]-dimethyl-silanyl}-benzene 在 红铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(dimethyl-phenyl-silanyl)-3,4-dimethyl-pyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted γ-Lactams by the [3+2] Annulation of α-Siloxy Allylic Silanes with Chlorosulfonyl Isocyanate

  摘要：

  A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.

  DOI：

  10.1021/ol060596g
• 作为产物：
  描述：

  苯基二甲基氯硅烷 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 {[(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enyl]-dimethyl-silanyl}-benzene
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted γ-Lactams by the [3+2] Annulation of α-Siloxy Allylic Silanes with Chlorosulfonyl Isocyanate

  摘要：

  A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.

  DOI：

  10.1021/ol060596g

文献信息

• Stereoselective Synthesis of Highly Substituted γ-Lactams by the [3+2] Annulation of α-Siloxy Allylic Silanes with Chlorosulfonyl Isocyanate
  作者：Antonio Romero、K. A. Woerpel

  DOI：10.1021/ol060596g

  日期：2006.5.1

  A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.