phenylmethyl (2R,4S)-4-bromo-2-(1-methylethyl)-5-oxo-4-(phenylmethyl)-1,3-dioxolane-2-carboxylate | 408516-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylmethyl (2R,4S)-4-bromo-2-(1-methylethyl)-5-oxo-4-(phenylmethyl)-1,3-dioxolane-2-carboxylate
• 英文别名: benzyl (2R,4S)-4-benzyl-4-bromo-5-oxo-2-propan-2-yl-1,3-dioxolane-2-carboxylate
• CAS: 408516-40-5
• 化学式: C₂₁H₂₁BrO₅
• 分子量: 433.299
• InChiKey: HQMHMQJVFLFZCY-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenylmethyl (2R,4S)-4-bromo-2-(1-methylethyl)-5-oxo-4-(phenylmethyl)-1,3-dioxolane-2-carboxylate 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以100%的产率得到phenylmethyl (2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylate
  参考文献：
  名称：

  Guignardic Acid, a Novel Type of Secondary Metabolite Produced by the Endophytic FungusGuignardia sp.: Isolation, Structure Elucidation, and Asymmetric Synthesis

  摘要：

  A UV-guided fractionation of the AcOEt extract of the fermentation broth of Guignardia sp., an endophytic fungus from the leaves of the tropical tree Spondias mombin, resulted in the identification of the new metabolite (-)-(2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid (1), isolated as NHT4+ salt 1a. The metabolite 1 was designated (-)-(S)-guignardic acid. This first member of a new class of natural compounds contains a dioxolanone moiety formed by fusion of 2-oxo-3-phenylpropanoic acid (phenylpyruvic acid) and 3-methyl-2-oxobutanoic acid (dimethylpyruvic acid), products of the oxidative deamination of phenylalanine and valine. respectively. The structure of 1a was deduced from spectral data (UV. IR, MS. H-1- and C-13-NMR) and confirmed by asymmetric synthesis.

  DOI：

  10.1002/1522-2675(20011219)84:12<3766::aid-hlca3766>3.0.co;2-z
• 作为产物：
  描述：

  sodium 3-methyl-2-oxobutyrate 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 三氟化硼乙醚 作用下， 以 四氯化碳 为溶剂， 反应 2.67h， 生成 phenylmethyl (2R,4S)-4-bromo-2-(1-methylethyl)-5-oxo-4-(phenylmethyl)-1,3-dioxolane-2-carboxylate
  参考文献：
  名称：

  Guignardic Acid, a Novel Type of Secondary Metabolite Produced by the Endophytic FungusGuignardia sp.: Isolation, Structure Elucidation, and Asymmetric Synthesis

  摘要：

  A UV-guided fractionation of the AcOEt extract of the fermentation broth of Guignardia sp., an endophytic fungus from the leaves of the tropical tree Spondias mombin, resulted in the identification of the new metabolite (-)-(2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid (1), isolated as NHT4+ salt 1a. The metabolite 1 was designated (-)-(S)-guignardic acid. This first member of a new class of natural compounds contains a dioxolanone moiety formed by fusion of 2-oxo-3-phenylpropanoic acid (phenylpyruvic acid) and 3-methyl-2-oxobutanoic acid (dimethylpyruvic acid), products of the oxidative deamination of phenylalanine and valine. respectively. The structure of 1a was deduced from spectral data (UV. IR, MS. H-1- and C-13-NMR) and confirmed by asymmetric synthesis.

  DOI：

  10.1002/1522-2675(20011219)84:12<3766::aid-hlca3766>3.0.co;2-z