(S)-methyl 3-phenyl-5-methyl-4,5-dihydroisoxazole-5-carboxylate | 17647-40-4

• 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: (S)-methyl 3-phenyl-5-methyl-4,5-dihydroisoxazole-5-carboxylate
• 英文别名: methyl (5S)-5-methyl-3-phenyl-4H-1,2-oxazole-5-carboxylate
• CAS: 17647-40-4；128358-34-9
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: QSPIPGHKVZNURH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-methyl 3-phenyl-5-methyl-4,5-dihydroisoxazole-5-carboxylate 在 sodium hydroxide 、 phosphate buffer 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 生成 (S)-methyl 3-phenyl-5-methyl-4,5-dihydroisoxazole-5-carboxylate 、 (R)-methyl 3-phenyl-5-methyl-4,5-dihydroisoxazole-5-carboxylate 、 (R)-5-Methyl-3-phenyl-4,5-dihydro-isoxazole-5-carboxylic acid 、 (5S)-5-methyl-3-phenyl-4H-1,2-oxazole-5-carboxylic acid
  参考文献：
  名称：

  Resolution of ?2-isoxazoline-5-carboxylates by a protease fromAspergillus Oryzae providing masked synthons for enantiopure ?-aminoalcohols and related structures

  摘要：

  A series of racemic DELTA2-isoxazolinecarboxylates have been synthesized and subjected to enzymatic hydrolysis by a protease from Aspergillus oryzae in a two-phase system. Out of these compounds only isoxazoline-5-carboxylates unsubstituted at C-4 were hydrolyzed. Thus, from 3-ethoxycarbonyl-, 3-methyl-, and 3-phenyl-DELTA2-isoxazoline-5-carboxylates the corresponding (R)-configurated carboxylic acids are obtained. In contrast, an additional methyl group at C-5 changes the steric course of the hydrolysis to give predominantly the (S)-acid. The enantioselectivities obtained are in the range of E = 5-35.

  DOI：

  10.1007/bf00811865