(Z)-3-Bromo-4-hydroxy-2-pentenoate | 132334-65-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-Bromo-4-hydroxy-2-pentenoate
• 英文别名: methyl (Z)-3-bromo-4-hydroxy-2-pentenoate；methyl (Z)-3-bromo-4-hydroxypent-2-enoate
• CAS: 132334-65-7
• 化学式: C₆H₉BrO₃
• 分子量: 209.04
• InChiKey: PWRIHENLFLUDCJ-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl 2,3-pentadienoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 16.0h， 以4%的产率得到(Z)-3-Bromo-4-hydroxy-2-pentenoate
  参考文献：
  名称：

  Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

  摘要：

  Treatment of gamma-monosubstituted allenic esters with N-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c), and bromobeckerelide (2a).

  DOI：

  10.1021/jo00111a045

文献信息

• Synthesis of 5-alkyl-4-bromo-5-hydroxy-2(5)-furanones and 5-alkylidene-4-bromo-2(5)-furanones
  作者：J. Font、A. Gracia、P. de March

  DOI：10.1016/s0040-4039(00)97887-0

  日期：1990.1
• Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide
  作者：Pedro de March、Josep Font、Antonio Gracia、Zheng Qingying

  DOI：10.1021/jo00111a045

  日期：1995.3

  Treatment of gamma-monosubstituted allenic esters with N-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (1a), acetoxyfimbrolide (1c), and bromobeckerelide (2a).