3-羟基-4-萘-1-基氧基丁腈 | 20804-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-羟基-4-萘-1-基氧基丁腈
• 英文名称: 3-hydroxy-4-(1-naphthyloxy)butanenitrile
• 英文别名: 3-Hydroxy-4-(1-naphthyloxy)butyronitrile；3-hydroxy-4-naphthalen-1-yloxybutanenitrile
• CAS: 20804-76-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: ASZJWZSLVVSBAH-UHFFFAOYSA-N

物化性质

• 沸点：
  467.0±25.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)
• 溶解度：
  易溶于可溶于氯仿、甲醇

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

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3-羟基-4-萘-1-基氧基丁腈 在 sodium hydroxide 、 Novocym 435 (Candida antarctica lipase B) 、 双氧水 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (S)-3-hydroxy-4-(1-naphthyloxy)butanoic acid
  参考文献：
  名称：

  β-羟基腈高效脂肪酶催化的动力学拆分和动态动力学拆分。绝对构型的校正和向手性β-羟基酸和γ-氨基醇的转化

  摘要：

  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。

  DOI：

  10.1002/1615-4169(200210)344:9<947::aid-adsc947>3.0.co;2-z
• 作为产物：
  描述：

  3-(1-萘氧基)-1,2-环氧丙烷 、 氰化钠 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 3-羟基-4-萘-1-基氧基丁腈
  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

• Synthesis and antiinflammatory activity of 4-(p-biphenylyl)-3-hydroxybutyric acid and related compounds
  作者：D. I. Barron、P. T. Bysouth、R. W. Clarke、A. R. Copley、O. Stephenson、D. K. Vallance、A. M. Wild

  DOI：10.1021/jm00312a008

  日期：1968.11
• A facile preparation of (±)-β-hydroxy nitriles and their enzymatic resolution with lipases
  作者：Ahmed Kamal、G.B. Ramesh Khanna

  DOI：10.1016/s0957-4166(01)00058-1

  日期：2001.3

  A simple and efficient method for the preparation of racemic 4-aryloxy-3-hydroxybutanenitriles is described, Lipase mediated kinetic resolution in organic media was then utilised to effect enantioseparation. Lipases from different sources were screened in the resolution reaction using a number of organic solvents. Enantiomeric excesses of up to 99%, were obtained by employing lipase from Pseudomonas cepacia in di-iso-propyl ether medium. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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
• Synthesis of δ-Hydroxy-β-oxo Esters using Sonochemical Blaise Reaction
  作者：Kesavaram Narkunan、Biing-Jiun Uang

  DOI：10.1055/s-1998-2213

  日期：1998.12
• 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.