6-hydroxy-2,3-dicyanonaphthalene | 78119-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hydroxy-2,3-dicyanonaphthalene
• 英文别名: 6-hydroxynaphthalodinitrile；6-Hydroxynaphthalene-2,3-dicarbonitrile
• CAS: 78119-80-9
• 化学式: C₁₂H₆N₂O
• 分子量: 194.192
• InChiKey: ZQERRZUQGYVQBR-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C (decomp)(Solv: acetone (67-64-1))
• 沸点：
  491.3±30.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,3-dicyanonaphthalene 、 1-碘己烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 80.0h， 以55.8%的产率得到6-(hexyloxy)-2,3-dicyanonaphthalene
  参考文献：
  名称：

  Synthesis of Alkyl- and Alkyloxy-Substituted 2,3-Naphthalocyanines

  摘要：

  Four novel differently substituted 2,3-dicyanonaphthalenes (6-(hexyloxy)-2,3-dicyanonaphthalene (5), 5-(hexyloxy)-2,3-dicyanonaphthalene (11), 6,7-bis(hexyloxy)-2,3-dicyanonaphthalene (17), and 5,8-diheptyl-2,3-dicyanonaphthalene (22)) and the respective peripherally substituted (bis(tert-butylisocyano)-2,3-naphthalocyaninato)iron(II) compounds 23-26 were synthesized and characterized.

  DOI：

  10.1021/jo00130a031
• 作为产物：
  描述：

  3,4-dimethylphenyl benzoate 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium iodide 作用下， 以 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-hydroxy-2,3-dicyanonaphthalene
  参考文献：
  名称：

  Kopranenkov, V. N.; Makarova, E. A.; Luk'yanets, E. A., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 2, p. 303 - 306

  摘要：

  DOI：

文献信息

• Phthalocyanine-centred and naphthalocyanine-centred aryl ether dendrimers with oligo(ethyleneoxy) surface groups
  作者：Matthew Brewis、Madeleine Helliwell、Neil B. McKeown

  DOI：10.1016/s0040-4020(03)00436-8

  日期：2003.5

  The synthesis of the 1st, 2nd and 3rd generation phthalocyanine-centred and naphthalocyanine-centred poly(aryl ether) dendrimers possessing oligo(ethyleneoxy) surface groups is described. These materials are soluble in polar protic solvents. For both types of macrocycle, the tendency of the non-polar phthalocyanine core towards intermolecular cofacial aggregation is not reduced by peripheral dendritic substitution. However, the prohibition of cofacial aggregation can be achieved by placing the dendritic substituents at the axial sites of the silicon-containing macrocycle. A single crystal X-ray diffraction analysis of one of these compounds beautifully illustrates this concept. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Anomerically glycosylated zinc(II) naphthalocyanines
  作者：Zafar Iqbal、Alexey Lyubimtsev、Michael Hanack、Thomas Ziegler

  DOI：10.1016/j.tetlet.2009.07.127

  日期：2009.10

  in course of our work on sugar-substituted phthalocyanines (Pc's) for PDT applications, for the first time two macrocyclic Pc homologs, the anomerically tetraglucosylated Zn(II) naphthalocyanines 11 and 12 were synthesized and characterized. (C) 2009 Elsevier Ltd. All rights reserved.
• KOPRANENKOV V. N.; MAKAROVA E. A.; LUKYANETS E. A., ZH. ORGAN. XIMII, 1981, 17, HO 2, 358-361
  作者：KOPRANENKOV V. N.、 MAKAROVA E. A.、 LUKYANETS E. A.

  DOI：——

  日期：——
• Synthesis of Alkyl- and Alkyloxy-Substituted 2,3-Naphthalocyanines
  作者：Rainer Polley、Michael Hanack

  DOI：10.1021/jo00130a031

  日期：1995.12

  Four novel differently substituted 2,3-dicyanonaphthalenes (6-(hexyloxy)-2,3-dicyanonaphthalene (5), 5-(hexyloxy)-2,3-dicyanonaphthalene (11), 6,7-bis(hexyloxy)-2,3-dicyanonaphthalene (17), and 5,8-diheptyl-2,3-dicyanonaphthalene (22)) and the respective peripherally substituted (bis(tert-butylisocyano)-2,3-naphthalocyaninato)iron(II) compounds 23-26 were synthesized and characterized.
• Kopranenkov, V. N.; Makarova, E. A.; Luk'yanets, E. A., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 2, p. 303 - 306
  作者：Kopranenkov, V. N.、Makarova, E. A.、Luk'yanets, E. A.

  DOI：——

  日期：——