N-(4-hydroxy-2,6-dimethylphenyl)-2-phenylacetamide | 321947-80-2

• 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: N-(4-hydroxy-2,6-dimethylphenyl)-2-phenylacetamide
• 英文别名: N-(4-hydroxy-2,6-dimethylphenyl)-2-phenyl-acetamide
• CAS: 321947-80-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: GLNZFCGCCZTAEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxy-2,6-dimethylphenyl)-2-phenylacetamide 在 lead(IV) tetraacetate 、 溶剂黄146 作用下， 生成 N-(2,6-dimethyl-4-oxo-1-propoxycyclohexa-2,5-dien-1-yl)-2-phenylacetamide
  参考文献：
  名称：

  Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols

  摘要：

  Steric strain in the C=N-C fragment in 3,5-disubstituted N-acyl-1,4-benzoquinone monoimines, unlike their N-arylsulfonyl analogs, leads to increase of the C=N-C angle above 130A degrees or twisting of the double C=N bond and loss of planarity of the quinoid ring. This structural transformation enhances the reactivity of the C=N bond so that 1,2-addition of alcohols becomes possible with formation of sterically unstrained cyclohexadienone structure with sp (3)-hybridized C-4 carbon atom. DOI: 10.1134/S1070428013010107

  DOI：

  10.1134/s1070428013010107
• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 、 苯乙酰氯 在 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到N-(4-hydroxy-2,6-dimethylphenyl)-2-phenylacetamide
  参考文献：
  名称：

  Synthesis and structure of N-aryl(phenoxy, benzylidene)acetyl-1,4-benzoquinone monoimines

  摘要：

  New N-aryl(phenoxy, benzylidene)acetyl-1,4-benzoquinone monoimines were synthesized by reaction of aminophenols with arylacetyl, phenoxyacetyl, and cinnamoyl chlorides in dimethylformamide-acetic acid (1: 3) in the presence of anhydrous sodium acetate. Structural parameters of the products and their probable biological activity were determined.

  DOI：

  10.1134/s1070428012100089

文献信息

• Reaction of N-[aryl(benzylidene, phenoxy)acetyl]-1,4-benzoquinone imines with sodium 4-methylbenzenesulfinate
  作者：S. A. Konovalova、A. P. Avdeenko、V. M. Vasil’eva、A. L. Yusina

  DOI：10.1134/s1070428014100054

  日期：2014.10

  The reaction of N-[aryl(phenoxy, benzylidene)acetyl]-1,4-benzoquinone imines with sodium 4-methylbenzenesulfinates takes different addition patterns, depending on the LUMO energy and charge distribution over the quinoid ring of the initial quinone imine.
• Synthesis and structure of N-aryl(phenoxy, benzylidene)acetyl-1,4-benzoquinone monoimines
  作者：A. P. Avdeenko、S. A. Konovalova、V. M. Vasil’eva、O. V. Shishkin、G. V. Palamarchuk、V. N. Baumer

  DOI：10.1134/s1070428012100089

  日期：2012.10

  New N-aryl(phenoxy, benzylidene)acetyl-1,4-benzoquinone monoimines were synthesized by reaction of aminophenols with arylacetyl, phenoxyacetyl, and cinnamoyl chlorides in dimethylformamide-acetic acid (1: 3) in the presence of anhydrous sodium acetate. Structural parameters of the products and their probable biological activity were determined.
• Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols
  作者：A. P. Avdeenko、S. A. Konovalova、V. M. Vasil’eva、G. V. Palamarchuk、V. N. Baumer、O. V. Shishkin

  DOI：10.1134/s1070428013010107

  日期：2013.1

  Steric strain in the C=N-C fragment in 3,5-disubstituted N-acyl-1,4-benzoquinone monoimines, unlike their N-arylsulfonyl analogs, leads to increase of the C=N-C angle above 130A degrees or twisting of the double C=N bond and loss of planarity of the quinoid ring. This structural transformation enhances the reactivity of the C=N bond so that 1,2-addition of alcohols becomes possible with formation of sterically unstrained cyclohexadienone structure with sp (3)-hybridized C-4 carbon atom. DOI: 10.1134/S1070428013010107