1-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-3-phenylurea | 1174550-27-6

• 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: 1-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-3-phenylurea
• 英文别名: 3,5-dimethyl-N-phenylamino-carbonyl-1,4-benzoquinone monoimine；N-phenylaminocarbonyl-2,6-dimethyl-1,4-benzoquinone imine；1-(2,6-Dimethyl-4-oxocyclo-hexa-2,5-dien-1-ylidene)-3-phenylurea
• CAS: 1174550-27-6
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: RXKOHOHFNZSBCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-3-phenylurea 在 sodium azide 、 溶剂黄146 作用下， 以86%的产率得到1-(3-azido-4-hydroxy-2,6-dimethylphenyl)-3-phenylurea
  参考文献：
  名称：

  Reaction of N-arylcarbamoyl-1,4-benzoquinone imines with sodium azide

  摘要：

  N-Arylcarbamoyl-1,4-benzoquinone imines reacted with sodium azide in completely regioselective fashion according to the 1,4-addition pattern with formation of 1-(3-azido-4-hydroxyphenyl)-3-arylureas. The reaction of N-arylcarbamoyl-2,6-dichloro-3,5-dimethyl-1,4-benzoquinone imines with sodium azide afforded N-arylcarbamoyl-2,6-diazido-3,5-dimethyl-1,4-benzoquinone imines as a result of nucleophilic substitution of the chlorine atoms.

  DOI：

  10.1134/s1070428014030075
• 作为产物：
  描述：

  1-(4-hydroxy-2,6-dimethylphenyl)-3-phenylurea 在 lead(IV) tetraacetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以52%的产率得到1-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-3-phenylurea
  参考文献：
  名称：

  Synthesis and structure of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines

  摘要：

  New N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines were synthesized by reaction of isocyanates with the corresponding substituted 4-aminophenols, and their structure was determined on the basis of H-1 and C-13 NMR spectra and X-ray diffraction data.

  DOI：

  10.1134/s1070428008120075

文献信息

• Reaction of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone monoimines with alcohols
  作者：A. P. Avdeenko、S. A. Konovalova、A. G. Sergeeva、G. V. Palamarchuk、O. V. Shishkin

  DOI：10.1134/s1070428009050054

  日期：2009.5

  Reactions of N-alkyl(aryl)aminocarbonyl-3,5-dimethyl-1,4-benzoquinone monoimines with alcohols led to the formation of products of 1,2-addition, quinolide compounds. They are the final products in reactions with alkyl derivatives, but in event of aryl derivatives they underwent cyclization with the subsequent elimination of the alcohol molecule to provide 4,7a-dimethyl-1-aryl-7,7a-dihydro-1H-benzimidazole-2,6-diones.
• Reaction of N-arylcarbamoyl-1,4-benzoquinone imines with sodium arenesulfinates
  作者：S. A. Konovalova、A. P. Avdeenko、A. G. Sergeeva、Yu. V. Menafova

  DOI：10.1134/s1070428014090103

  日期：2014.9

  N-Arylcarbamoyl-1,4-benzoquinone imines possessing at least one free ortho position with respect to the carbonyl carbon atom in the quinoid ring react with sodium arenesulfinates according to the nucleophilic 1,4-addition pattern with complete regioselectivity. If both ortho positions are occupied, the reaction gives a mixture of products where the major ones are 1,6- and 6,1-adducts formed according to the radical ion mechanism.