(+/-)-5-(2-hydroxy-2-p-nitrophenylethyl)-3-methylisoxazole

• 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: (+/-)-5-(2-hydroxy-2-p-nitrophenylethyl)-3-methylisoxazole
• 英文别名: 5-(2-hydroxy-2-p-nitrophenyl)ethyl-3-methylisoxazole；2-(3-Methyl-5-isoxazolyl)-1-(4-nitrophenyl)ethanol；2-(3-methyl-1,2-oxazol-5-yl)-1-(4-nitrophenyl)ethanol
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: AECJXJNIBOGGGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二甲基异唑 、 对硝基苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以5%的产率得到(+/-)-5-(2-hydroxy-2-p-nitrophenylethyl)-3-methylisoxazole
  参考文献：
  名称：

  Synthesis of optically active β′-hydroxy-β-enaminoketones via enzymatic resolution of carbinols derived from 3,5-disubstituted isoxazoles

  摘要：

  The preparation of several enantiomerically pure beta'-hydroxy-beta-enaminoketones from the corresponding isoxazolic carbinols, which have been obtained by enzymatic kinetic resolution of the racemic beta-hydroxy-isoxazoles catalyzed by lipases? is described. The enzymatic transesterification of racemic (+/-)-5-(2-hydroxy-propyl)-3-methylisoxazole 3a, and racemic (+/-)-5-(2-hydroxy-2-p-tolylethyl)-3-methylisoxazole 3d, has been studied with respect to the influence of experimental variables such as the used enzyme, the acylating agent or the solvent on the enantioselectivity of the reaction. After the reductive cleavage of the isoxazolic ring of the enantiopure carbinols, (R)- and (S)-2-amino-4-oxo-2-hepten-6-ol, (R)- and (S)-5, and (R)-2-amino-6-p-tolyl-4-oxo-2-hexen-6-ol, (R)-7 with an enantiomeric excess > 98% were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00225-1

文献信息

• Lewis Acid Mediated Addition of Tri-n-Butylstannylmethylisoxazole with Aldehydes
  作者：Makoto Yamamoto、Kazumi Ohtsuka、Keiki Kishikawa、Shigeo Kohmoto

  DOI：10.1080/00397919608003577

  日期：1996.6

  Lewis acid mediated addition of 5-(tri-n-butylstannyl)methyl-3-methylisoxazole and its analogues with aldehydes have been carried out Corresponding 5-(beta-hydroxy)ethylisoxazoles were obtained in moderate yields, without ring opening of the isoxazole.
• Synthesis of optically active β′-hydroxy-β-enaminoketones via enzymatic resolution of carbinols derived from 3,5-disubstituted isoxazoles
  作者：José Antonio Fuentes、Alicia Maestro、Ana Ma Testera、José Manuel Báñez

  DOI：10.1016/s0957-4166(00)00225-1

  日期：2000.6

  The preparation of several enantiomerically pure beta'-hydroxy-beta-enaminoketones from the corresponding isoxazolic carbinols, which have been obtained by enzymatic kinetic resolution of the racemic beta-hydroxy-isoxazoles catalyzed by lipases? is described. The enzymatic transesterification of racemic (+/-)-5-(2-hydroxy-propyl)-3-methylisoxazole 3a, and racemic (+/-)-5-(2-hydroxy-2-p-tolylethyl)-3-methylisoxazole 3d, has been studied with respect to the influence of experimental variables such as the used enzyme, the acylating agent or the solvent on the enantioselectivity of the reaction. After the reductive cleavage of the isoxazolic ring of the enantiopure carbinols, (R)- and (S)-2-amino-4-oxo-2-hepten-6-ol, (R)- and (S)-5, and (R)-2-amino-6-p-tolyl-4-oxo-2-hexen-6-ol, (R)-7 with an enantiomeric excess > 98% were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.