N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)acetamide | 89345-80-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)acetamide
• 英文别名: 4-O-Methyl-4-methyl-p-benzoquinol N-acetylimine
• CAS: 89345-80-2
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XQTCVFJWQFJONG-LUAWRHEFSA-N

物化性质

• 沸点：
  277.7±50.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)acetamide 在 acid 作用下， 以 水 为溶剂， 生成 4-甲氧基-4-甲基-2,5-环己二烯-1-酮
  参考文献：
  名称：

  Isolation, characterization, and rearrangement of cis- and trans-N-acetyl-2-amino-5,6-dimethoxy-5-methylcyclohexa-1,3-diene. Models for the proposed precursors of meta-substitution products from carcinogenic aromatic amines

  摘要：

  DOI：

  10.1021/ja00320a045
• 作为产物：
  描述：

  N-(4-甲基苯基)乙酰氧肟酸 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)acetamide
  参考文献：
  名称：

  Isolation, characterization, and rearrangement of cis- and trans-N-acetyl-2-amino-5,6-dimethoxy-5-methylcyclohexa-1,3-diene. Models for the proposed precursors of meta-substitution products from carcinogenic aromatic amines

  摘要：

  DOI：

  10.1021/ja00320a045

文献信息

• Preparation of quinol N-acyl- and quinol ether imines via anodic oxidation of para-substituted anilide derivatives
  作者：John S. Swenton、Timothy N. Biggs、William M. Clark

  DOI：10.1021/jo00073a016

  日期：1993.10

  Anodic oxidation of N-benzoyl-4-methylaniline in 5 % aqueous methanol in the presence of sodium bicarbonate affords two major products: 4-methoxy-4-methylbenzoquinol N-benzoylimine, 8a, and a dimer, 4-[N-benzoyl-N-(4-methylphenyl)amino]-4-methylbenzoquinol N-benzoylimine, 9. The ratio of these two products was temperature dependent, and conditions were developed for preparing 8a and 9 in good yield. Using the conditions developed for 8a, the anodic methoxylation of N-benzoyl and acetyl derivatives of 4-ethyl- and 4-sec-butyl-4-phenylaniline and 2-aminofluorene derivatives was performed. The yields of the N-benzoyl derivatives of the 4-methoxy-4-substituted-benzoquinol imines were 46-80%, while the N-acetyl derivatives gave lower yields. When the anodic oxidation was performed using 30% water/acetonitrile or 10 % water/tetrahydrofuran, the 4-alkylbenzoquinol N-benzoylimine derivatives were obtained. The yields of these anodic hydroxylation reactions were lower than those of the corresponding methoxylations for all systems studied. In addition, the 4-alkylbenzoquinol N-benzoylimine derivatives were much more labile. Two methods were developed for conversion of the 4-methoxy-4-substituted-benzoquinol N-acylimines to the 4-methoxy-4-substituted-benzoquinol N-alkylimines. Finally, the especially labile 4-hydroxy-4-phenylbenzoquinol N-acetylimine was prepared for the first time from the readily available N-benzoyl derivative.
• GASSMAN, P. G.;GRANRUD, J. E., J. AMER. CHEM. SOC., 1984, 106, N 8, 2448-2449
  作者：GASSMAN, P. G.、GRANRUD, J. E.

  DOI：——

  日期：——
• Isolation, characterization, and rearrangement of cis- and trans-N-acetyl-2-amino-5,6-dimethoxy-5-methylcyclohexa-1,3-diene. Models for the proposed precursors of meta-substitution products from carcinogenic aromatic amines
  作者：Paul G. Gassman、John E. Granrud

  DOI：10.1021/ja00320a045

  日期：1984.4