bromofluoroketene isopropyl trimethylsilyl acetal | 222724-27-8

• 英文名称: bromofluoroketene isopropyl trimethylsilyl acetal
• 英文别名: (2-Bromo-2-fluoro-1-propan-2-yloxyethenoxy)-trimethylsilane
• CAS: 222724-27-8
• 化学式: C₈H₁₆BrFO₂Si
• 分子量: 271.202
• InChiKey: DYUTVQHJXWPGJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异戊醛 、 bromofluoroketene isopropyl trimethylsilyl acetal 在 Masamune's catalyst 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 isopropyl anti-(-)-2-bromo-2-fluoro-3-hydroxy-5-methylhexanoate 、 (2R,3R)-2-Bromo-2-fluoro-3-hydroxy-5-methyl-hexanoic acid isopropyl ester 、 isopropyl syn-2-bromo-2-fluoro-3-hydroxy-5-methylhexanoate
  参考文献：
  名称：

  Enantioselective aldol reaction with bromofluoroketene silyl acetals

  摘要：

  The aldol reaction of aldehydes with bromofluoroketene ethyl trimethylsilyl acetal in the presence of a catalytic amount of a chiral Lewis acid at -78 degrees C provides a mixture of the corresponding syn- and anli-alpha-bromo-alpha-fluoro-beta-hydroxy esters with high enantioselectivities (up to 99% ee). Reaction temperature has a great influence on the stereoselectivity. The aldol reaction at -20 degrees C proceeds with high enantio- and diasteteoselectivities to preferentially afford the anti-aldols having opposite signs of optical rotation to those at -78 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00005-8
• 作为产物：
  描述：

  三甲基氯硅烷 、 isopropyl dibromofluoroacetate 在 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以48%的产率得到bromofluoroketene isopropyl trimethylsilyl acetal
  参考文献：
  名称：

  Enantioselective aldol reaction with bromofluoroketene silyl acetals

  摘要：

  The aldol reaction of aldehydes with bromofluoroketene ethyl trimethylsilyl acetal in the presence of a catalytic amount of a chiral Lewis acid at -78 degrees C provides a mixture of the corresponding syn- and anli-alpha-bromo-alpha-fluoro-beta-hydroxy esters with high enantioselectivities (up to 99% ee). Reaction temperature has a great influence on the stereoselectivity. The aldol reaction at -20 degrees C proceeds with high enantio- and diasteteoselectivities to preferentially afford the anti-aldols having opposite signs of optical rotation to those at -78 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00005-8