(5SR,1'RS,2'E)-3-bromo-5-[1-hydroxy-2-methylbut-2-enyl]-5H-furan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5SR,1'RS,2'E)-3-bromo-5-[1-hydroxy-2-methylbut-2-enyl]-5H-furan-2-one
• 英文别名: (2S)-4-bromo-2-[(E,1R)-1-hydroxy-2-methylbut-2-enyl]-2H-furan-5-one
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: PKQZDOFLQHJRQD-IQPYVPGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 4-溴2(5H)-呋喃酮 在 三甲基氯硅烷 、 三乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以80%的产率得到(5SR,1'SR,2'E)-3-bromo-5-[1-hydroxy-2-methylbut-2-enyl]-5H-furan-2-one
  参考文献：
  名称：

  Simple Diastereoselectivity of the BF₃·OEt₂-Catalyzed Vinylogous Mukaiyama Aldol Reaction of 2-(Trimethylsiloxy)furans with Aldehydes

  摘要：

  A comprehensive scan of the transition state space for the reaction of 2-(trimethylsiloxy)furan and methacrolein (24 combinations) offered a satisfactory explanation of the high like diastereoselectivity obtained experimentally in the Mukaiyama vinylogous aldol reaction of these and related partners. It was determined that the syn-gamma-hydroxyalkylbutenolides are formed preferentially following a g(+) orientation of the two reactants with the aldehyde in the s-trans conformation. Diastereoselectivity is shown to be caused by a combination of subtle effects favoring the formation of the like product.

  DOI：

  10.1021/jo0501339

文献信息

• Simple Diastereoselectivity of the BF₃·OEt₂-Catalyzed Vinylogous Mukaiyama Aldol Reaction of 2-(Trimethylsiloxy)furans with Aldehydes
  作者：Carlos Silva López、Rosana Álvarez、Belén Vaz、Olalla Nieto Faza、Ángel R. de Lera

  DOI：10.1021/jo0501339

  日期：2005.4.1

  A comprehensive scan of the transition state space for the reaction of 2-(trimethylsiloxy)furan and methacrolein (24 combinations) offered a satisfactory explanation of the high like diastereoselectivity obtained experimentally in the Mukaiyama vinylogous aldol reaction of these and related partners. It was determined that the syn-gamma-hydroxyalkylbutenolides are formed preferentially following a g(+) orientation of the two reactants with the aldehyde in the s-trans conformation. Diastereoselectivity is shown to be caused by a combination of subtle effects favoring the formation of the like product.