2,3-dimethyl-5-ethoxycarbonyl-5-phenyl-3-isoxazoline | 899833-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-dimethyl-5-ethoxycarbonyl-5-phenyl-3-isoxazoline
• CAS: 899833-44-4
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: LRYLSHMXXDSKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,3-dimethyl-5-ethoxycarbonyl-5-phenyl-4,5-dihydroisoxazolium methylsulfate 、 氰化钠 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2,3-dimethyl-5-ethoxycarbonyl-5-phenyl-3-isoxazoline 、 cis-2,3-dimethyl-3-cyano-5-ethoxycarbonyl-5-phenylisoxazolidine 、 trans-2,3-dimethyl-3-cyano-5-ethoxycarbonyl-5-phenylisoxazolidine
  参考文献：
  名称：

  Chemical and biochemical transformations of 5-ethoxycarbonyl-5-phenyl-2-isoxazolines

  摘要：

  The salts, 2-methyl-5,5-disubstituted 4,5-dihydroisoxazolium methylsulfates comprising various substituents at the C-3 carbon atom were subjected to transformations. The structure of applied compounds permitted to monitor the effect of this factor on the transformation course of the 2-isoxazoline ring. The nucleophilic addition of cyanide anion to the selected salts enabled the obtaining of a next heterocyclic system of changed physicochemical and biological properties in comparison to the starting 2-isoxazolines. The diastereoselective hydrolysis of the cyanide group in 2-isoxazolidines by the bacteria strain Rhodococcus rhodochrous PCM 909 leads to the obtaining of a racemic mixture of the trans-hydroxyacid. The introduction of new functional groups into the heterocyclic ring made these compounds attractive objects for further chemical and microbial transformations and to study their biological activity.

  DOI：

  10.1016/j.farmac.2005.07.003