(2S)-4-amino-4-phenyl-1,2-butanediol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-4-amino-4-phenyl-1,2-butanediol
• 英文别名: (2S)-4-amino-4-phenylbutane-1,2-diol
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MWXNEPQRLUVWRY-RGURZIINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-硝基苯基乙酸酯 、 (2S)-4-amino-4-phenyl-1,2-butanediol 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4R)-4-acetamido-4-phenyl-1,2-butanediol 、 (2S,4S)-(-)-4-acetamido-4-phenyl-1,2-butanediol
  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

文献信息

• Resolution of ?2-isoxazoline-5-carboxylates by a protease fromAspergillus Oryzae providing masked synthons for enantiopure ?-aminoalcohols and related structures
  作者：S. Yang、W. Hayden、H. Griengl

  DOI：10.1007/bf00811865

  日期：1994.4

  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.