(4S,5'R)-4-(3'-bromo-4',5'-dihydroisoxazol-5'-yl)-2,2-dimethyl-N-tert-butoxycarbonyloxazolidine | 151069-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5'R)-4-(3'-bromo-4',5'-dihydroisoxazol-5'-yl)-2,2-dimethyl-N-tert-butoxycarbonyloxazolidine
• 英文别名: tert-butyl (4S)-4-[(5R)-3-bromo-4,5-dihydro-1,2-oxazol-5-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 151069-84-0
• 化学式: C₁₃H₂₁BrN₂O₄
• 分子量: 349.225
• InChiKey: FYORQHOQPZBLLJ-DTWKUNHWSA-N

物化性质

• 熔点：
  82-84 °C(Solvent: Hexane)
• 沸点：
  382.9±52.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  60.36
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5'R)-4-(3'-bromo-4',5'-dihydroisoxazol-5'-yl)-2,2-dimethyl-N-tert-butoxycarbonyloxazolidine 、 苯甲醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以4.4 g的产率得到
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

  摘要：

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.

  DOI：

  10.1021/jm701394a
• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 3-噁唑烷羧酸,4-乙烯基-2,2-二甲基-,1,1-二甲基乙基酯,(4R)- 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以4.37 g的产率得到(4S,5'R)-4-(3'-bromo-4',5'-dihydroisoxazol-5'-yl)-2,2-dimethyl-N-tert-butoxycarbonyloxazolidine
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

  摘要：

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.

  DOI：

  10.1021/jm701394a