(R)-3-hydroxy-4-(1-naphthyloxy)butanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3-hydroxy-4-(1-naphthyloxy)butanenitrile
• 英文别名: (R)-3-hydroxy-4-(1-naphthoxy)butanenitrile；(3R)-3-hydroxy-4-naphthalen-1-yloxybutanenitrile
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: ASZJWZSLVVSBAH-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(1-萘氧基)-1,2-环氧丙烷 在 Pseudomonas Cepacia lipase on diatomite 作用下， 以 乙醇 、 异丙醚 、 水 为溶剂， 反应 66.0h， 生成 (R)-3-hydroxy-4-(1-naphthyloxy)butanenitrile
  参考文献：
  名称：

  New chemoenzymatic pathway for β-adrenergic blocking agents

  摘要：

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.015

文献信息

• Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. Correction of Absolute Configuration and Transformation to Chiral β-Hydroxy Acids and γ-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1002/1615-4169(200210)344:9<947::aid-adsc947>3.0.co;2-z

  日期：2002.10

  Chemoenzymatic dynamic kinetic resolution of β-hydroxy nitriles 1 has been carried out using Candida antarctica lipase B and a ruthenium catalyst. The use of a hydrogen source to depress ketone formation in the dynamic kinetic resolution yields the corresponding acetates 2 in good yield and high enantioselectivity. It is shown that the ruthenium catalyst and the enzyme can be recycled when used in

  β-羟基腈1的化学酶动力学动力学拆分已使用南极假丝酵母脂肪酶B和钌催化剂进行。使用氢源以动态动力学拆分抑制酮的形成以良好的产率和高的对映选择性产生相应的乙酸酯2。结果表明，钌催化剂和酶在单独的反应中使用时可以循环使用。我们还报告了从1和2制备各种对映体纯的β-羟基酸衍生物和γ-氨基醇的情况。后一化合物也用于建立1和2的正确绝对构型。
• Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.3.co;2-5

  日期：2001.8
• New chemoenzymatic pathway for β-adrenergic blocking agents
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、Venkatesh Tekumalla、R. Ramu

  DOI：10.1016/j.tetasy.2005.02.015

  日期：2005.4

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.