(R)-5-(2-hydroxypropyl)-3-methylisoxazole | 296240-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-5-(2-hydroxypropyl)-3-methylisoxazole
• 英文别名: (2R)-1-(3-methyl-1,2-oxazol-5-yl)propan-2-ol
• CAS: 296240-61-4
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: HXTYDQUEZYJCNE-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-(2-hydroxypropyl)-3-methylisoxazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以88%的产率得到2-amino-4-oxo-2-hepten-6-ol
  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
• 作为产物：
  描述：

  3,5-二甲基异唑 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 (R)-5-(2-hydroxypropyl)-3-methylisoxazole
  参考文献：
  名称：

  通过微生物氧化还原的手性（R）-和（S）-1-杂芳基-和1-芳基-2-丙醇

  摘要：

  描述了制备各种杂芳基丙醇2a – g和相应的丙烷3a – g作为微生物氧化还原的起始原料的制备方法。外消旋丙醇2a – g的动力学拆分是通过用假单胞菌和嗜热脂肪芽孢杆菌[（R）-醇，ee 74-100％]氧化获得的。用3-（2-羟丙基）三氟甲基苯7（44％，ee 100％的（R）-醇6）获得了相似的结果。丙烷3a – d和的还原3克含面包酵母和其他真菌的（S）醇（ee 100％）。也可以通过还原1- [3-（三氟甲基）苯基] -2-丙酮7获得纯的（S）醇。1 - [（4,4-二甲基）-2-（Δ 2）唑啉基] -2-丙酮3E和1 [2-（Δ 2）-thiazolinyl）-2-丙酮3F不降低。（S）-5-（2-羟丙基）-3-甲基异唑2d和（S）-2-（2-羟丙基）-4-甲基噻唑2g的杂环被解封为同手性烯胺酮8（78％）和受保护的β-羟基醛9（73％）。将（R）-3-（2-羟丙基）三氟甲基苯6

  DOI：

  10.1016/s0957-4166(98)00215-8

文献信息

• Homochiral (R)- and (S)-1-heteroaryl- and 1-aryl-2-propanols via microbial redox
  作者：Marco Fogagnolo、Pier Paolo Giovannini、Alessandra Guerrini、Alessandro Medici、Paola Pedrini、Nicola Colombi

  DOI：10.1016/s0957-4166(98)00215-8

  日期：1998.7

  Preparation of various heteroaryl propanols 2a–g and of the corresponding propanones 3a–g as starting materials for microbial redox is described. The kinetic resolution of the racemic propanols 2a–g is obtained via oxidation with Pseudomonas paucimobilis and Bacillus stearothermophilus [(R)-alcohols, ee 74–100%]. Similar results are achieved with 3-(2-hydroxypropyl)trifluoromethylbenzene 7 (44%, ee

  描述了制备各种杂芳基丙醇2a – g和相应的丙烷3a – g作为微生物氧化还原的起始原料的制备方法。外消旋丙醇2a – g的动力学拆分是通过用假单胞菌和嗜热脂肪芽孢杆菌[（R）-醇，ee 74-100％]氧化获得的。用3-（2-羟丙基）三氟甲基苯7（44％，ee 100％的（R）-醇6）获得了相似的结果。丙烷3a – d和的还原3克含面包酵母和其他真菌的（S）醇（ee 100％）。也可以通过还原1- [3-（三氟甲基）苯基] -2-丙酮7获得纯的（S）醇。1 - [（4,4-二甲基）-2-（Δ 2）唑啉基] -2-丙酮3E和1 [2-（Δ 2）-thiazolinyl）-2-丙酮3F不降低。（S）-5-（2-羟丙基）-3-甲基异唑2d和（S）-2-（2-羟丙基）-4-甲基噻唑2g的杂环被解封为同手性烯胺酮8（78％）和受保护的β-羟基醛9（73％）。将（R）-3-（2-羟丙基）三氟甲基苯6
• 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.