3,4,5-trimethyl-4-nitrocyclohexa-2,5-dien-1-one | 32591-49-4

• 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: 3,4,5-trimethyl-4-nitrocyclohexa-2,5-dien-1-one
• 英文别名: 3,4,5-trimethyl-4-nitrocyclohexa-2,5-dienone；4-Nitro-3,4,5-trimethyl-cyclohexa-2,5-dien-1-on；3,4,5-Trimethyl-4-nitrocyclohexadienon；3,4,5-Trimethyl-4-nitro-2,5-cyclohexadien-1-one
• CAS: 32591-49-4
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: NKEQNJQBOUAFPO-UHFFFAOYSA-N

物化性质

• 熔点：
  64.5-66 °C
• 沸点：
  303.2±42.0 °C(Predicted)
• 密度：
  1.16±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：
  0.44
• 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：

  3,4,5-trimethyl-4-nitrocyclohexa-2,5-dien-1-one 以100%的产率得到
  参考文献：
  名称：

  CLEMENS A. H.; HARTSHORN M. P.; RICHARDS K. E.; WRIGHT G. J., AUSTRAL. J. CHEM. , 1977, 30, NO 1, 113-121

  摘要：

  DOI：
• 作为产物：
  描述：

  5-acetoxy-1,2,3-trimethylbenzene 在 硝酸 、 乙酸酐 作用下， 生成 3,4,5-trimethyl-4-nitrocyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  芳烃的乙酰氧基化。第六部分 在溴，乙酰氧基和甲氧基芳烃的硝化反应中形成4-硝基环己-2,5-二烯酮

  摘要：

  5-取代的半亚甲基（1,2,3-三甲基苯）（3a-c）和4-取代的邻二甲苯（3d-f）与硝酸-乙酸酐的反应生成了4-硝基环己-2,5-二壬烯（5a）和（5b）除正常替代产品外。

  DOI：

  10.1039/j29710001212

文献信息

• Hartshorn, Michael P.; Judd, Maurice C.; Vannoort, Richard W., Australian Journal of Chemistry, 1989, vol. 42, # 5, p. 689 - 697
  作者：Hartshorn, Michael P.、Judd, Maurice C.、Vannoort, Richard W.、Wright, Graeme J.

  DOI：——

  日期：——
• Photochemical Nitration by Tetranitromethane. Part XXVI. Adduct Formation in the Photochemical Reaction of 1,2,3-Trimethylbenzene: the Formation of 'Double' Adducts Including Nitronic Esters.
  作者：Craig P. Butts、Lennart Eberson、Michael P. Hartshorn、Ward T. Robinson、David J. Timmerman-Vaughan、Dawson A. W. Young、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0029

  日期：——

  The photolysis of the charge-transfer complex of 1,2,3-trimethylbenzene and tetranitromethane gives a complex mixture of products, most of which arise by initial attack of trinitromethanide ion on the unsubstituted ring positions at C4(C6) and C5 of the radical cation of 1,2,3-trimethylbenzene. The products 7-19 are adducts resulting directly or indirectly from the addition of the elements of tetranitromethane to 1,2,3-trimethylbenzene, and the trinitromethyl aromatic compounds 22-25 are formed by eliminations from intermediate adducts. Six adducts are simple 'single' adducts, nitro-trinitromethyl adducts 7, 8, 10-12, while nitro cycloadduct 9 is formed by cycloaddition of nitro-trinitromethyl adduct 8. The remaining addition products are 'double' adducts, formed by secondary addition reactions initiated by attack of nitrogen dioxide on the buta-1,3-diene system of 'single' adducts, and include trinitro-trinitromethyl compounds 13 and 15, the hydroxy-dinitro-trinitromethyl compound 14, and a group of four nitronic esters 16-19 formed by nitro-denitrocyclization of initially formed hydroxy-trinitromethyl and nitro-trinitromethyl 'single' adducts. Minor amounts of other products are formed including two nitrodienones 21 and 22, and the rearrangement product, 4,5,6-trimethyl-2-nitrophenol (28), and the 2,3,4-trimethyl- and 3,4,5-trimethylnitrobenzenes 26 and 27.The modes of formation of the above products are discussed, and X-ray crystal structure determinations are reported for compounds 9, 13, 14, 18, 19, 22 and 29.