2,4-dimethyl-4-nitrocyclohexa-2,5-dienone | 77815-19-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone
• 英文别名: 2,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-one
• CAS: 77815-19-1
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: XZAZOMWOOPLHIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.0±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-4-nitrocyclohexa-2,5-dienone 反应 1.0h， 生成 2,4-二甲基-6-硝基苯酚
  参考文献：
  名称：

  Formation of dienones on the reaction of cresols, xylenols, and 2-naphthol with nitrogen dioxide: Observation of keto tautomers of nitrophenols

  摘要：

  DOI：

  10.1016/s0040-4039(00)82064-x
• 作为产物：
  描述：

  2,4-二甲基苯酚 在 二氧化氮 作用下， 以 氘代氯仿 为溶剂， 反应 0.75h， 生成 2,4-dimethyl-4-nitrocyclohexa-2,5-dienone
  参考文献：
  名称：

  Formation of dienones on the reaction of cresols, xylenols, and 2-naphthol with nitrogen dioxide: Observation of keto tautomers of nitrophenols

  摘要：

  DOI：

  10.1016/s0040-4039(00)82064-x

文献信息

• Cross, Gordon G.; Fischer, Alfred; Henderson, George N., Canadian Journal of Chemistry, 1984, vol. 62, p. 1446 - 1451
  作者：Cross, Gordon G.、Fischer, Alfred、Henderson, George N.、Smyth, Trevor A.

  DOI：——

  日期：——
• Ridd, John H.; Trevellick, Susan; Sandall, John P. B., Journal of the Chemical Society. Perkin transactions II, 1992, # 9, p. 1535 - 1540
  作者：Ridd, John H.、Trevellick, Susan、Sandall, John P. B.

  DOI：——

  日期：——
• Photochemical Nitration by Tetranitromethane. Part XXXVII. Adduct Formation and the Regiochemistry of Attack of Trinitromethanide Ion on Radical Cations in the Photochemical Reactions of 2-Methyl-, 2,3-Dimethyl- and 2,4-Dimethylanisoles.
  作者：Craig P. Butts、Lennart Eberson、Michael P. Hartshorn、Ward T. Robinson、David J. Timmerman-Vaughan、Lauri Niinistö、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0073

  日期：——

  The photolysis of the charge transfer (CT) complex of tetranitromethane and 2-methylanisole 2 in dichloromethane at 20 degrees C gives the epimeric 1-methoxy-6-methyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 8 and 9 in addition to 2-methyl-4-trinitromethylanisole (3) and 2-methyl-4-nitroanisole (4). In acetonitrile the yields of compound 4 and adducts 8 and 9 are significantly higher. Similar reaction of 2,3-dimethylanisole (6) in dichloromethane gave nitrotrinitromethyl adducts 10 and 11, hydroxy-trinitromethyl adducts 12 and 13, 2,3-dimethyl-5-trinitromethylanisole (14), 4-methoxy-2,3-dimethylbenzonitrile N-oxide (15), 2,3-dimethyl-4-trinitromethylanisole (16), 2,3-dimethyl-4-nitroanisole (17), 2,3-dimethyl-4,6-dinitrophenol (18), 3-methoxy-4,5-dimethyl-benzoic acid (19) and the hydroxy dinitro compound (20).The photolysis of the CT complex of 2,4-dimethylanisole (7) with tetranitromethane in dichloromethane gave the epimeric 1-methoxy-4,6-dimethyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 21 and 22, together with 4,6-dimethyl-3-trinitromethylanisole (23), 4,6-dimethyl-2-nitrophenol (24), 4,6-dimethyl-2-trinitromethylanisole (25), 4,6-dimethyl-3-nitroanisole (26), 4,6-dimethyl-2-nitroanisole (27) and 4,6-dimethyl-4-nitrocyclohexa-2,5-dienone (28).The modes of formation of the above products are discussed, including the effects of the reaction solvent on those processes. The X-ray crystal structure of 1-methoxy-2-methyl-c-6-nitro-r-3-trinitromethylcyclohexa-1,4-diene (9) is reported.
• FISCHER A.; HENDERSON G. N., TETRAHEDRON LETT., 1980, 21, NO 49, 4661-4662
  作者：FISCHER A.、 HENDERSON G. N.

  DOI：——

  日期：——
• CROSS, G. G.;FISCHER, A.;HENDERSON, G. N.;SMYTH, T. A., CAN. J. CHEM., 1984, 62, N 8, 1446-1451
  作者：CROSS, G. G.、FISCHER, A.、HENDERSON, G. N.、SMYTH, T. A.

  DOI：——

  日期：——