2-((3-acetylphenoxy)methyl)benzonitrile | 1016691-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3-acetylphenoxy)methyl)benzonitrile
• 英文别名: 2-[(3-Acetylphenoxy)methyl]benzonitrile
• CAS: 1016691-05-6
• 化学式: C₁₆H₁₃NO₂
• mdl: MFCD09929748
• 分子量: 251.285
• InChiKey: WXFCMXLDMBFQMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((3-acetylphenoxy)methyl)benzonitrile 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-{3-[(2-cyanobenzyl)oxy]phenyl}-2,4-dioxobutanoic acid
  参考文献：
  名称：

  Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase

  摘要：

  alpha,gamma-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the gamma position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.

  DOI：

  10.1021/jm0342109
• 作为产物：
  描述：

  (E)-3-[3-[(2-cyanophenyl)methoxy]phenyl]prop-2-enoic acid 在 iron(II) chloride 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以50.8 mg的产率得到2-((3-acetylphenoxy)methyl)benzonitrile
  参考文献：
  名称：

  Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C–H methylation

  摘要：

  铁催化的α，β-不饱和羧酸的串联脱羧氧化反应，实现了醛的C-H甲基化，用于制备多样化的甲基酮，并可应用于复杂小分子的晚期修饰。

  DOI：

  10.1039/d1cc01536b

文献信息

• Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C–H methylation
  作者：Pei-Xue Gong、Fangning Xu、Lu Cheng、Xu Gong、Jie Zhang、Wei-Jin Gu、Wei Han

  DOI：10.1039/d1cc01536b

  日期：——

  The iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C–H methylation for preparing diversified methyl ketones is developed and can be applied to the late-stage modification of complex small molecules.

  铁催化的α，β-不饱和羧酸的串联脱羧氧化反应，实现了醛的C-H甲基化，用于制备多样化的甲基酮，并可应用于复杂小分子的晚期修饰。
• Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase
  作者：Vincenzo Summa、Alessia Petrocchi、Paola Pace、Victor G. Matassa、Raffaele De Francesco、Sergio Altamura、Licia Tomei、Uwe Koch、Philippe Neuner

  DOI：10.1021/jm0342109

  日期：2004.1.1

  alpha,gamma-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the gamma position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.