5,8-dihydroxy-2,6,7-trimethyl-1,4-naphthoquinone | 32741-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2,6,7-trimethyl-1,4-naphthoquinone
• 英文别名: trimethylnaphthazarin；1,4-Naphthalenedione, 5,8-dihydroxy-2,3,7-trimethyl-；5,8-dihydroxy-2,6,7-trimethylnaphthalene-1,4-dione
• CAS: 32741-24-5
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: ISQDKVIPTQHNSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,6-trimethyl-4a,5,8,8a-tetrahydro-1,4-naphthoquinone 在 chromium(VI) oxide 、 sodium hydroxide 作用下， 以 溶剂黄146 为溶剂， 生成 5,8-dihydroxy-2,6,7-trimethyl-1,4-naphthoquinone
  参考文献：
  名称：

  Structural Study of the Methylnaphthazarins. X-Ray Structure of the Tetramethylnaphthazarin, a Charge Transfer Complex

  摘要：

  尝试了甲基取代萘嗪的合成和1H NMR分析。将取代基和环质子的化学位移与其二乙酸酯中的化学位移进行比较，然后与环的醌类或苯类性质相关。四甲基萘醌（2,3,6,7-四甲基-5,8-二羟基-1,4-萘醌）的 X 射线衍射分析表明，它以固态形式存在，作为与其自身中心对称的电荷转移络合物。该化合物在 Ibam 空间群中结晶，具有尺寸为 a=17.479(1)、b=9.983(1)、c=6.752(1) Å 的斜方晶胞，晶胞中有四个分子。该晶体由沿 c 轴堆叠的分子构成，两个重叠分子之间的晶面距离为 3.38 Å。

  DOI：

  10.1246/bcsj.59.3957

文献信息

• The Reductive Dehalogenation of Halo-Substituted Naphthazarins and Quinizarins as a Simple Route to Parent Compounds
  作者：Victor Ph. Anufriev、Galina V. Malinovskaya、Vyacheslav L. Novikov、Nadezhda N. Balanyova、Sergey G. Polonik

  DOI：10.1080/00397919808007029

  日期：1998.6

  Abstract By the reaction of 2-chloro-3-alkyl-, 2,3-dichloro(dibromo)-, trichloro-(tribromo)-and tetrachloro(tetrabromo)-naphthazarins and 2,3-dichloroquinizarin with Fe/HOAc followed by oxidation with an air in a mild basic conditions the corresponding naphthazarins and quinizarin were obtained in good to excellent yields.

  摘要 通过 2-氯-3-烷基-、2,3-二氯（二溴）-、三氯-（三溴）-和四氯（四溴）-萘并和 2,3-二氯喹吖啶与 Fe/HOAc 反应，然后氧化在温和碱性条件下的空气中，以良好至极好的收率获得了相应的萘并芴素。
• Sartori, Giovanni; Bigi, Franca; Goffredi, Gino, Journal of Chemical Research, Miniprint, 1993, # 8, p. 2061 - 2079
  作者：Sartori, Giovanni、Bigi, Franca、Goffredi, Gino、Maggi, Raimondo、Portioli, Roberto、Casnati, Giuseppe

  DOI：——

  日期：——
• Structural Study of the Methylnaphthazarins. X-Ray Structure of the Tetramethylnaphthazarin, a Charge Transfer Complex
  作者：José-Gonzalo Rodriguez、Alfonso De Pablo、Pilar Smith-Verdier、Feliciana Florencio、Severino Garcia-Blanco

  DOI：10.1246/bcsj.59.3957

  日期：1986.12

  The synthesis and analysis by 1H NMR of the methyl substituted naphthazarins were attempted. The chemical shifts of the substituents and of the ring protons were compared with those in their diacetates and were then correlated with the quinonoid or benzenoid nature of the rings. X-Ray diffraction analysis of tetramethylnaphthazarin, 2,3,6,7-tetramethyl-5,8-dihydroxy-1,4-naphthoquinone, has shown that this exists, in solid state, as a centrosymmetric charge-transfer complex with itself. The compound crystallizes in the Ibam space group, with an orthorhombic cell of dimensions a=17.479(1), b=9.983(1), c=6.752(1) Å, and four molecules in the unit cell. The crystal is built from molecules stacked up the c-axis and the interplanar distance between two overlapping molecules is 3.38 Å.

  尝试了甲基取代萘嗪的合成和1H NMR分析。将取代基和环质子的化学位移与其二乙酸酯中的化学位移进行比较，然后与环的醌类或苯类性质相关。四甲基萘醌（2,3,6,7-四甲基-5,8-二羟基-1,4-萘醌）的 X 射线衍射分析表明，它以固态形式存在，作为与其自身中心对称的电荷转移络合物。该化合物在 Ibam 空间群中结晶，具有尺寸为 a=17.479(1)、b=9.983(1)、c=6.752(1) Å 的斜方晶胞，晶胞中有四个分子。该晶体由沿 c 轴堆叠的分子构成，两个重叠分子之间的晶面距离为 3.38 Å。