9H-fluoren-9-ylmethyl N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate | 831172-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate
• CAS: 831172-01-1
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: VZCILVRIRWAZPZ-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  9H-fluoren-9-ylmethyl N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]carbamate 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.12 g的产率得到(S)-1-羟基-1-(4-羟基苯基)-2-氨基乙烷
  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：

  Butyric acid (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-1-(4-hydroxy-phenyl)-ethyl ester 在 Candida antarctica lipase B 、 异丙醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 384.0h， 以0.36 g的产率得到9H-fluoren-9-ylmethyl N-[(2S)-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