3-hydroxy-4-(4-methylphenoxy)butanenitrile | 59961-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-4-(4-methylphenoxy)butanenitrile
• 英文别名: Butanenitrile, 3-hydroxy-4-(4-methylphenoxy)-
• CAS: 59961-92-1
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: LZUDSOVUHANCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-(4-methylphenoxy)butanenitrile 以86%的产率得到
  参考文献：
  名称：

  FAURAN C.; DOUZON C., EUR. J. MED. CHEM., 1976, 11, NO 1, 73-74

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium cyanide 、 对叔丁基苯基1-(2,3-环氧)丙基醚 在 2,2'-(1,2-phenylenediylbisnitrilomethylidine)bis(4-hydroxyphenolato)nickel(II) 作用下， 以 乙腈 为溶剂， 反应 1.08h， 以85%的产率得到3-hydroxy-4-(4-methylphenoxy)butanenitrile
  参考文献：
  名称：

  Highly regioselective conversion of epoxides to β-hydroxy nitriles using metal(II) Schiff base complexes as new catalysts under mild conditions

  摘要：

  Epoxides undergo efficient ring opening with potassium cyanide in acetonitrile in the presence of metal Schiff base complexes as catalysts. This method was carried out under neutral and mild conditions with both high yields and high regioselectivity within a short period of time. Thus, several beta-hydroxy nitriles, useful intermediates for the synthesis of biologically active molecules, were easily obtained at room temperature. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.10.019

文献信息

• A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent
  作者：Najmedin Azizi、Zahra Rahimi、Masoumeh Alipour

  DOI：10.1039/c5ra06176h

  日期：——

  Magnetic Fe3O4 nanoparticles in deep eutectic solvents (DESs) have been regard as excellent catalysts for highly efficient cyanosilylation of various aldehydes and epoxides using trimethylsilyl cyanide TMSCN in high yields with excellent selectivity. Fe3O4 nanoparticles were synthesized and applied as a catalyst for the preparation of a wide variety of cyanohydrins (α-hydroxy nitriles and β-hydroxy

  在低共熔溶剂（DES）中的磁性Fe 3 O 4纳米粒子已被视为出色的催化剂，可使用三甲基甲硅烷基氰化物TMSCN高产率，高选择性地对各种醛和环氧化物进行高效氰基硅烷化。合成了Fe 3 O 4纳米颗粒，并将其用作催化剂，用于在容易获得的尿素-氯化胆碱深度低共熔溶剂DES中制备各种氰醇（α-羟基腈和β-羟基腈），这是最有希望的对环境有益的，具有成本效益的绿色溶剂。磁性DES在非常温和的反应条件下运行，可以很容易地回收利用，而不会显着降低其催化活性。
• Metal(II) Schiff base complexes as catalysts for the high-regioselective conversion of epoxides to β-hydroxy nitriles in glycol solvents
  作者：Hossein Naeimi、Mohsen Moradian

  DOI：10.1139/v06-158

  日期：2006.11.1

  A facile preparation of 3-hydroxy propanenitrile derivatives is described involving ring opening of epoxides with potassium cyanide in glycol solvents in the presence of Schiff base complexes as catalysts. This method occurs under neutral and mild conditions with high yields and high regioselectivity. Thus, several β-Hydroxy nitriles, useful intermediates toward biologically-active molecules, are easily obtained at room temperature.Key words: β-hydroxy nitrile, Schiff base, epoxide, glycol, catalyst.

  本文介绍了一种简便的 3-羟基丙腈衍生物制备方法，该方法涉及环氧化物与氰化钾在乙二醇溶剂中，在希夫碱络合物作为催化剂存在下的开环反应。该方法在中性温和的条件下进行，具有高产率和高区域选择性。因此，可在室温下轻松获得几种 β-羟基腈，它们是生物活性分子的有用中间体。
• 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.
• WYRICK S. D.; PIANTADOSI C., J. MED. CHEM., 1978, 21, NO 4, 386-390
  作者：WYRICK S. D.、 PIANTADOSI C.

  DOI：——

  日期：——
• Highly regioselective conversion of epoxides to β-hydroxy nitriles using metal(II) Schiff base complexes as new catalysts under mild conditions
  作者：Hossein Naeimi、Azam Karshenas

  DOI：10.1016/j.poly.2012.10.019

  日期：2013.1

  Epoxides undergo efficient ring opening with potassium cyanide in acetonitrile in the presence of metal Schiff base complexes as catalysts. This method was carried out under neutral and mild conditions with both high yields and high regioselectivity within a short period of time. Thus, several beta-hydroxy nitriles, useful intermediates for the synthesis of biologically active molecules, were easily obtained at room temperature. (C) 2012 Elsevier Ltd. All rights reserved.