N-(2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide | 321941-05-3

• 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-(2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide
• 英文别名: N-(2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2-phenylacetamide
• CAS: 321941-05-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: POCTVHBJSXRFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide 、 sodium 4-methylbenzenesulfinate 以 溶剂黄146 为溶剂， 以97%的产率得到N-[4-hydroxy-2,5-dimethyl-3-(4-methylbenzenesulfonyl)phenyl]-2-phenylacetamide
  参考文献：
  名称：

  Reaction of N-[aryl(benzylidene, phenoxy)acetyl]-1,4-benzoquinone imines with sodium 4-methylbenzenesulfinate

  摘要：

  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.

  DOI：

  10.1134/s1070428014100054
• 作为产物：
  描述：

  N-(4-hydroxy-2,5-dimethylphenyl)-2-phenylacetamide 在 lead(IV) tetraacetate 作用下， 以 溶剂黄146 为溶剂， 生成 N-(2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide
  参考文献：
  名称：

  Reaction of N-[aryl(benzylidene, phenoxy)acetyl]-1,4-benzoquinone imines with sodium 4-methylbenzenesulfinate

  摘要：

  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.

  DOI：

  10.1134/s1070428014100054

文献信息

• 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.
• Thiocyanation of N-[phenyl(benzylidene, phenoxy)acetyl]-substituted 1,4-benzoquinone monoimines
  作者：S. A. Konovalova、A. P. Avdeenko、V. M. Vasil’eva、S. A. Goncharova

  DOI：10.1134/s1070428014110220

  日期：2014.11

  Thiocyanation of N-[aryl(phenoxy, benzylidene)acetyl]-substituted 1,4-benzoquinone monoimines afforded benzo[d][1,3]oxathiol-2-ones and benzo[d]oxazole-2(3H)-thiones. The direction of the reaction is governed by the energy of the intermediate species forming on the addition of the thiocyanate anion by the nitrogen atom under the charge control or by the sulfur atom under the orbital control.
• Reaction of N-phenyl(benzylidene, phenoxy)acetyl-1,4-benzoquinone imines with sodium azide
  作者：S. A. Konovalova、A. P. Avdeenko、V. M. Vasil’eva、S. A. Goncharova

  DOI：10.1134/s1070428014030087

  日期：2014.3

  N-Phenyl(benzylidene, phenoxy)acetyl-1,4-benzoquinone imines reacted with sodium azide to give the corresponding 1,4-addition products, N-(4-hydroxyphenyl) carboxamides. Quantum chemical calculations showed that the initial step in the examined reaction is addition of azide ion to neutral quinone imine molecule.