N-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide | 831171-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide
• 英文别名: N-[(2R)-2-Hydroxy-2-(3-hydroxyphenyl)ethyl]butanamide；N-[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]butanamide
• CAS: 831171-91-6
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: PTCREKLAHHCVKK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide 在 盐酸 作用下， 以 甲醇 为溶剂， 以0.280 g的产率得到(R)-norphenylephrine
  参考文献：
  名称：

  Enantiomers of adrenaline-type amino alcohols by Burkholderia cepacia lipase-catalyzed asymmetric acylation

  摘要：

  Burkholderia cepacia lipase-catalyzed acylation with butanoic anhydride was used for the preparation of pharmaceutically important norphenylephrine and octopamine enantiomers, all in 98% ee. Reactivity of the phenolic OH groups and easy racemization, especially in the case of octopamine, complicated optimization. For norphenylephrine, chemical N-acylation was fast and allowed the subsequent enzymatic benzylic acylation in situ. The preparation of the octopamine enantiomers became possible by using the N-Fmoc protected substrate and by the Candida antarctica lipase B-catalyzed deprotection of the OH groups before the N-deprotection was performed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.027
• 作为产物：
  描述：

  丁酸酐 、 N-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide 在 Tris-HCl buffer 、 Burkholderia cepacia lipase on Celite(R) 、 蔗糖 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 以0.692 g的产率得到N-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide
  参考文献：
  名称：

  Enantiomers of adrenaline-type amino alcohols by Burkholderia cepacia lipase-catalyzed asymmetric acylation

  摘要：

  Burkholderia cepacia lipase-catalyzed acylation with butanoic anhydride was used for the preparation of pharmaceutically important norphenylephrine and octopamine enantiomers, all in 98% ee. Reactivity of the phenolic OH groups and easy racemization, especially in the case of octopamine, complicated optimization. For norphenylephrine, chemical N-acylation was fast and allowed the subsequent enzymatic benzylic acylation in situ. The preparation of the octopamine enantiomers became possible by using the N-Fmoc protected substrate and by the Candida antarctica lipase B-catalyzed deprotection of the OH groups before the N-deprotection was performed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.027

文献信息

• Room Temperature Ionic Liquids in the Kinetic Resolution of Adrenaline-Type Aminoethanols byBurkholderia cepacia Lipase under Normal and Microwave Conditions
  作者：Katri Lundell、Toni Kurki、Maria Lindroos、Liisa T. Kanerva

  DOI：10.1002/adsc.200505049

  日期：2005.6

  The lipase PS-C II (lipase from Burkholderia cepacia immobilized on ceramic particles)-catalyzed acylations of N-acylated 2-amino-1-phenylethanol (rac-1) and N-acylated norphenylephrine (rac-2) have been studied in imidazolium- and pyridinium-based ionic liquids, in tert-butyl methyl ether (TBME) and in their mixtures. Enzymatic chemo- and enantioselectivities in the presence of hydrophobic EMIM⋅NTf2

  脂肪酶PS-C II（由脂肪酶洋葱伯克霍尔德菌固定在陶瓷颗粒）的催化的酰化Ñ -acylated 2-氨基-1-苯基乙醇（外消旋- 1）和Ñ -acylated甲苯福林（外消旋- 2）在咪唑鎓进行了研究-和基于吡啶鎓的离子液体，在叔丁基甲基醚（TBME）及其混合物中。在疏水性EMIM·NTf 2和亲水性EMIM·BF 4存在下，使用高底物浓度对酶的化学选择性和对映选择性进行了更详细的研究。rac- 1和rac-的制备规模动力学拆分在EMIM·NTf 2与TBME（2：1）的混合物中用丁酸乙烯酯2（均为0.45 M）分别花费9和27个小时。微波辅助的酰化外消旋- 1和外消旋2在EMIM⋅NTf存在2在正常条件下类似地进行到反应。