tert-butyl N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate | 831172-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tert-butyl N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate
• CAS: 831172-00-0
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: YGJBWOOFDAKLIF-NSHDSACASA-N

物化性质

• 沸点：
  444.6±40.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 奥克巴胺
  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 、 tert-butyl (2-hydroxy-2-(4-hydroxyphenyl)ethyl)carbamate 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 142.0h， 生成 tert-butyl N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate 、
  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