2-hydroxy-3-(4-methoxyphenyl)-2-methyl-propanenitrile | 198287-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-3-(4-methoxyphenyl)-2-methyl-propanenitrile
• 英文别名: 2-hydroxy-3-(4-methoxy-phenyl)-2-methyl-propionitrile；2-Hydroxy-3-(4-methoxy-phenyl)-2-methyl-propionitril；4-Methoxy-phenylaceton-cyanhydrin；2-Hydroxy-3-(4-methoxyphenyl)-2-methylpropanenitrile
• CAS: 198287-13-7
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: OVAMWICFUOUOKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  2-hydroxy-3-(4-methoxyphenyl)-2-methyl-propanenitrile 在 盐酸 、 水 作用下， 生成 2-hydroxy-3-(4-methoxy-phenyl)-2-methyl-propionic acid amide
  参考文献：
  名称：

  Le Brazidec, Bulletin de la Societe Chimique de France, 1922, vol. <4> 31, p. 261

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲氧基-2-(4-甲氧基苯基)-N-甲基乙酰胺 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-hydroxy-3-(4-methoxyphenyl)-2-methyl-propanenitrile
  参考文献：
  名称：

  用于 α- 和 β- 羟基酸位点选择性和立体发散合成的多功能生物催化 C(sp3)−H 氧官能化

  摘要：

  在此，α-酮戊二酸依赖性芳氧基链烷酸双加氧酶（AAD）被重新用于生物催化氧功能化中的应用。天然 AAD 的活性分析使得四种类型的α-和β-羟基酸的合成具有广泛、高效和良好的选择性。

  DOI：

  10.1002/anie.202305250

文献信息

• Synthesis of optically active cyanohydrins from aromatic ketones: evidence of an increased substrate range and inverted stereoselectivity for the hydroxynitrile lyase from Linum usitatissimum
  作者：Christopher Roberge、Fred Fleitz、David Pollard、Paul Devine

  DOI：10.1016/j.tetasy.2006.12.026

  日期：2007.2

  The synthesis of (R)- and (S)-cyanohydrins from a range of aromatic methyl and ethyl ketones, including the first examples from substituted variants of phenylacetone, benzylacetone and propiophenone, is described. Commercially available hydroxynitrile lyase (HNL) enzymes were used to catalyze the asymmetric addition of cyanide to the ketones, including the first successful application of the flax HNL (LuHNL) to the synthesis of any aromatic (S)-cyanohydrin. Both reaction yields and stereoselectivities were shown to be influenced by the carbon chain length between the ketone and phenyl functional groups, and the type of aromatic substitution present on the starting material. Substrates converted with the greatest degree of productivity and selectivity were phenylacetones with large, electron withdrawing meta-substituents, such as 3-Cl, 3-Br and 3-CF3 phenylacetones, from which cyanohydrins are formed with 93-99% ee and 61-71% yield. (c) 2007 Elsevier Ltd. All rights reserved.
• Le Brazidec, Bulletin de la Societe Chimique de France, 1922, vol. <4> 31, p. 261
  作者：Le Brazidec

  DOI：——

  日期：——
• Versatile Biocatalytic C(<i>sp</i>³)−H Oxyfunctionalization for the Site‐ Selective and Stereodivergent Synthesis of α‐ and β‐Hydroxy Acids
  作者：Yingle Mao、Weijie Zhang、Zunyun Fu、Yanqiong Liu、Lin Chen、Xin Lian、Dan Zhuo、Jiewei Wu、Mingyue Zheng、Cangsong Liao

  DOI：10.1002/anie.202305250

  日期：2023.8.14

  α-ketoglutarate-dependent aryloxyalkanoate dioxygenases (AADs) are repurposed for applications in biocatalytic oxyfunctionalization. Activity profiling of natural AADs enabled the synthesis of four types of α-and β-hydroxy acids with broad scope, high efficiency, and good selectivity.

  在此，α-酮戊二酸依赖性芳氧基链烷酸双加氧酶（AAD）被重新用于生物催化氧功能化中的应用。天然 AAD 的活性分析使得四种类型的α-和β-羟基酸的合成具有广泛、高效和良好的选择性。