N-(3,5-二甲基-4-氧代-1-环己-2,5-二烯亚基)乙酰胺 | 74827-85-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(3,5-二甲基-4-氧代-1-环己-2,5-二烯亚基)乙酰胺
• 中文别名: 环戊二烯并[b]吡咯-6-甲酚,八氢-1-甲基-,[3aS-(3a-α-,6-α-,6a-α-)]-(9CI)
• 英文名称: N-acetyl-3,5-dimethyl-p-benzoquinone imine
• 英文别名: Acetamide, N-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-；N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetamide
• CAS: 74827-85-3
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD00078877
• 分子量: 177.203
• InChiKey: VUPORYDINWWWKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-(3,5-二甲基-4-氧代-1-环己-2,5-二烯亚基)乙酰胺 在 水 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以41%的产率得到2,6-二甲基-2,5-环己二烯-1,4-二酮
  参考文献：
  名称：

  对乙酰氨基酚的毒性机理研究。N-乙酰基-2,6-二甲基和N-乙酰基3,5-二甲基-对苯醌亚胺的合成和反应。

  摘要：

  通过用四乙酸铅氧化由2，6-二甲基对乙酰氨基酚和3，5-二甲基对乙酰氨基酚制备N-乙酰基-2，6-二甲基-对苯醌亚胺和N-乙酰基-3，5-二甲基-对苯醌亚胺。N-乙酰基-2,6-二甲基-对苯醌亚胺与盐酸反应生成3'-氯-2'，6'-二甲基-4'-羟基乙酰苯胺，而乙硫醇，苯胺和乙醇生成四面体加合物除了亚胺碳。水得到2，6-二甲基-对苯醌。用N-乙酰基-3,5-二甲基-对苯醌亚胺，水和苯胺取代亚胺碳，生成2,6-二甲基-对苯醌和3,5-二甲基-N-苯基-对苯醌亚胺。乙硫醇得到3'.5'-二甲基-2'-（乙硫基）-4'-羟基乙酰苯胺。2,6-二甲基对乙酰氨基酚和3的毒性，在小鼠和大鼠中组织学检查了5-二甲基对乙酰氨基酚。3,5-二甲基对乙酰氨基酚的肾毒性稍强，但显示出与对乙酰氨基酚相似的肝毒性。2，6-二甲基对乙酰氨基酚与N-甲基对乙酰氨基酚一样，几乎没有组织损伤。

  DOI：

  10.1021/jm00185a001
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 盐酸 、 sodium hydroxide 、 1,1-二苯-2-苦基肼 、 sodium carbonate 、 sodium nitrite 、 对氨基苯磺酸 作用下， 以 甲醇 、 氘代乙腈 、 水 为溶剂， 反应 17.5h， 生成 N-(3,5-二甲基-4-氧代-1-环己-2,5-二烯亚基)乙酰胺
  参考文献：
  名称：

  DPPH radical scavenging activity of paracetamol analogues

  摘要：

  Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.098

文献信息

• Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines
  作者：C. Roger Fernando、Ian C. Calder、Kathryn N. Ham

  DOI：10.1021/jm00185a001

  日期：1980.11

  N-Acetyl-2,6-dimethyl-p-benzoquinone imine and N-acetyl-3,5-dimethyl-p-benzoquinone imine were prepared from 2,6-dimethylacetaminophen and 3,5-dimethylacetaminophen by oxidation with lead tetraacetate. Reaction of N-acetyl-2,6-dimethyl-p-benzoquinone imine with hydrochloric acid gave 3'-chloro-2',6'-dimethyl-4'-hydroxyacetanilide, whereas ethanethiol, aniline, and ethanol gave tetrahedral adducts resulting

  通过用四乙酸铅氧化由2，6-二甲基对乙酰氨基酚和3，5-二甲基对乙酰氨基酚制备N-乙酰基-2，6-二甲基-对苯醌亚胺和N-乙酰基-3，5-二甲基-对苯醌亚胺。N-乙酰基-2,6-二甲基-对苯醌亚胺与盐酸反应生成3'-氯-2'，6'-二甲基-4'-羟基乙酰苯胺，而乙硫醇，苯胺和乙醇生成四面体加合物除了亚胺碳。水得到2，6-二甲基-对苯醌。用N-乙酰基-3,5-二甲基-对苯醌亚胺，水和苯胺取代亚胺碳，生成2,6-二甲基-对苯醌和3,5-二甲基-N-苯基-对苯醌亚胺。乙硫醇得到3'.5'-二甲基-2'-（乙硫基）-4'-羟基乙酰苯胺。2,6-二甲基对乙酰氨基酚和3的毒性，在小鼠和大鼠中组织学检查了5-二甲基对乙酰氨基酚。3,5-二甲基对乙酰氨基酚的肾毒性稍强，但显示出与对乙酰氨基酚相似的肝毒性。2，6-二甲基对乙酰氨基酚与N-甲基对乙酰氨基酚一样，几乎没有组织损伤。
• Reaction of N-acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines with sodium arenesulfinates
  作者：S. A. Konovalova、A. P. Avdeenko、V. V. Pirozhenko、O. P. Ledeneva、A. A. Santalova

  DOI：10.1134/s1070428014090097

  日期：2014.9

  N-Acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines having no substituent in the 2- and/or 6-position of the quinoid ring react with sodium arenesulfinates preferentially according to the 1,4-addition pattern. The presence of an ArSO2N group favors radical ion reaction with formation of 1,6-addition products.

  根据1,4，在醌环的2-和/或6-位没有取代基的N-乙酰基和N- [1-（芳基磺酰亚胺基）乙基] -1,4-苯醌亚胺优先与芳烃亚磺酸钠反应-加法模式。ArSO 2 N基团的存在有利于自由基离子反应并形成1，6-加成产物。
• Congeners of acetaminophen and related compounds as substrates for fatty acid conjugation and their use in treatment of pain, fever and inflammation
  申请人：——

  公开号：US20040209959A1

  公开（公告）日：2004-10-21

  The present invention relates to new analgesic, antipyretic and/or anti-inflammatory compounds represented by the general formula X—Y, in which X is a benzyl group, a saturated or unsaturated cycloalkyl group (I,II) or a non-cyclic, straight or branched alkyl group (III,IV).

  本发明涉及通式 X-Y 所代表的新型镇痛、解热和/或消炎化合物，其中 X 是苄基、饱和或不饱和环烷基（I,II）或非环状、直链或支链烷基（III,IV）。
• Rat liver microsomal cytochrome P450-dependent oxidation of 3,5-disubstituted analogues of paracetamol
  作者：J. G. M. Bessems、J. M. Te Koppele、P. A. Van Dijk、L. L. P. Van Stee、J. N. M. Commandeur、N. P. E. Vermeulen

  DOI：10.3109/00498259609046740

  日期：1996.1

  1. The cytochrome P450-dependent binding of paracetamol and a series of 3,5-disubstituted paracetamol analogues (R = -F, -Cl, -Br, -I, -CH3, -C2H5, -iC(3)H(7)) have been determined with beta-naphthoflavone (beta NF)-induced rat liver microsomes and produced reverse type I spectral changes. K-s,K-app varied from 0.14 mM for 3,5-diiC(3)H(7)-paracetamol to 2.8 mM for paracetamol.2. All seven analogues underwent rat liver microsomal cytochrome P450-dependent oxidation, as reflected by the formation of GSSG in the presence of GSH. The GSSG-formation was increased in all cases upon pretreatment of rats by beta-naphthoflavone (beta NF) and was generally decreased upon pretreatment by phenobarbital (PB).3. Rat liver microsomal cytochrome P450 as well as horseradish peroxidase catalysed the formation of 3,5-disubstituted NAPQI analogues from the corresponding parent compounds, as identified by UV-spectrophotometry of the NAPQI analogues and by GC/MS detection of the following GSH-conjugates: 2-glutathione-S-yl-3,5-dimethyl-1,4-dihydroxybenzene, 2-glutathione-S-yl-3,5-dichloro-paracetamol, and 2-glutathione-S-yl-3,5-dibromo-paracetamol.4. In liver microsomal (beta NF-induced) incubations, apparent K,values, as determined for the cytochrome P450 catalysis-dependent oxidation of GSH, for seven 3,5-disubstituted paracetamol analogues (R = -F, -Cl, -Br, -I, -CH3, -C2H5, iC(3)H(7)) varied from 0.07 to 0.64 mM. Paracetamol exhibited an apparent K-m of 0.73 mM. Apparent V-max values for the cytochrome P450 catalysis dependent oxidation of GSH varied from 0.66 nmol min(-1) mg(-1)protein for paracetamol to 3.0 nmol min(-1) mg(-1) protein for 3,5-dimethyl-paracetamol.
• FERNANDO C. R.; CALDER I. C.; HAM K. N., J. MED. CHEM., 1980, 23, NO 11, 1153-1158
  作者：FERNANDO C. R.、 CALDER I. C.、 HAM K. N.

  DOI：——

  日期：——