N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide | 321962-96-3

• 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-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide
• 英文别名: 3,5-dimethyl-N-phenylacetyl-1,4-benzoquinone imine；N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2-phenylacetamide
• CAS: 321962-96-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: JWILCTPVZBLLKQ-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：

  丙醇 、 N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)phenylacetamide 以48%的产率得到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：

  N-(4-hydroxy-3,5-dimethylphenyl)-2-phenylacetamide 在 lead(IV) tetraacetate 、 溶剂黄146 作用下， 反应 0.17h， 以83%的产率得到N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)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.
• 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.