N-(4-hydroxy-3,5-dimethylphenyl)-4-methylbenzamide | 321694-41-1

• 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-3,5-dimethylphenyl)-4-methylbenzamide
• 英文别名: 4-amino-2,6-dimethyl-N-(4-methylbenzoyl)phenol；N-(4-hydroxy-3,5-dimethylphenyl)-4-methyl-benzamide
• CAS: 321694-41-1
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: BBBPAGQKDWKIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  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-3,5-dimethylphenyl)-4-methylbenzamide 在 氯 作用下， 以 溶剂黄146 为溶剂， 生成 2,6-dimethyl-N-(4-methylbenzoyl)-3-chloro-1,4-benzoquinone monoimine
  参考文献：
  名称：

  Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms

  摘要：

  At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans-and syn-scheme.

  DOI：

  10.1134/s1070428009110128
• 作为产物：
  描述：

  2,6-dimethyl-N-(4-methylbenzoyl)-1,4-benzoquinone monoimine 在 potassium thioacyanate 作用下， 以 溶剂黄146 为溶剂， 以73%的产率得到N-(4-hydroxy-3,5-dimethylphenyl)-4-methylbenzamide
  参考文献：
  名称：

  Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl)benzimidoyl]-1,4-benzoquinone imines

  摘要：

  Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-benzoxathiol-2-ones as final products.

  DOI：

  10.1134/s1070428009030105

文献信息

• Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids
  作者：A. P. Avdeenko、S. A. Konovalova、D. A. Roman’kov、K. S. Burmistrov、V. M. Nichvoloda、O. V. Shishkin、R. I. Zubatyuk、G. V. Palamarchuk

  DOI：10.1134/s1070428009010084

  日期：2009.1

  The regioselectivity in the reactions of N-arylsulfonyl-2,6-dialkyl-1,4-benzoquinone imines with arenesulfinic acids (1,6-, 6,1-, or 6,3-addition) is determined by steric factor, while in the reactions of N-aroyl-1,4-benzoquinone imines electronic effect of substituents in the quinoid ring is crucial. The reactions of N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinone imines with arenesulfinic acids follow mainly the 1,4-addition pattern. N-(N-Arylsulfonylbenzimidoyl)-1,4-benzoquinone imines are capable of reacting in a way similar to both N-arylsulfonyl and N-aroyl derivatives.
• Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Ludchenko、G. V. Palamarchuk、O. V. Shishkin

  DOI：10.1134/s1070428009110128

  日期：2009.11

  At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans-and syn-scheme.
• Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl)benzimidoyl]-1,4-benzoquinone imines
  作者：A. P. Avdeenko、V. V. Pirozhenko、S. A. Konovalov、D. A. Roman’kov、G. V. Palamarchuk、O. V. Shishkinc

  DOI：10.1134/s1070428009030105

  日期：2009.3

  Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-benzoxathiol-2-ones as final products.