phthiocoloxime | 80690-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phthiocoloxime
• 英文别名: 2-hydroxy-3-methyl-1,4-naphthoquinone-1-oxime；3-methyl-2-hydroxy-1,4-naphthoquinone-1-oxime；3-methyl-2-hydroxy-4-naphthoquinone-1-oxime；phthiocol oxime；2-hydroxy-3-methyl-[1,4]naphthoquinone-1-oxime；2-Hydroxy-3-methyl-[1,4]naphthochinon-1-oxim
• CAS: 80690-05-7
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: POCHNIQSYBETHH-UHFFFAOYSA-N

物化性质

• 沸点：
  384.3±42.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.89
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phthiocoloxime 在 sodium perchlorate 、 magnesium 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 3-hydroxy-2-methyl-1,4-naphthoquinone 4-monoxime Mg(II)-complex
  参考文献：
  名称：

  Kamini; Sindhwani, S. K.; Singh, R. P., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1981, vol. 20, # 10, p. 1040 - 1042

  摘要：

  DOI：
• 作为产物：
  描述：

  3-hydroxy-2-methyl-1,4-naphthoquinone 4-monoxime Mg(II)-complex 在 sodium perchlorate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 phthiocoloxime
  参考文献：
  名称：

  Kamini; Sindhwani, S. K.; Singh, R. P., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1981, vol. 20, # 10, p. 1040 - 1042

  摘要：

  DOI：

文献信息

• Energetics of model compounds of water oxidizing complex containing quinone cofactors
  作者：A. V. Todkary、S. B. Zaware、D. R. Thube、J. V. Yakhmi、S. Y. Rane

  DOI：10.1007/s10973-005-0748-9

  日期：2005.7

  To reveal reaction mechanism of PS-II, the reaction products of photolysis may be compared with their thermolytic products. According to required molecular assemblies in manganese clusters at WOC of PS-II, we have strategically synthesized dimers (M-1, M-2), trimers (M-3A, M-3B) and tetramer (M-4) using spin carrier imino-phenol functionalized ligands viz. Lawsone Oxime (L-1) and Phthiocol Oxime (L-2) of naturally occurring quinones .These are characterized by elemental analyses, thermogravimetric analyses, differential thermal analyses, powder X-ray diffraction and infrared spectroscopy. Stabilization energies for molecular associations of ligands in various redox and stereoisomeric forms via hydrogen bondings are compared with thermal energies required for their expulsion from the coordination polymers calculated with the help of Coats and Redfern’s relation of rising temperatures. Activation energy required for establishing tetramer (M-4) and dimer (M-2) in coordination sphere by counter ion using same synthetic route is found to be comparable (~37.48±1 kJ mol-1). Quantitized energies from TG-DTA data for valence tautomers of redox active ligands play significant role in formation of resultant model compound. viz. tetramer, dimer of dimer and trimer. The role of oxo, acetato and spin carrier ligands in model cluster compounds are proposed with respect to their expulsion energies.

  为了揭示 PS-II 的反应机制，可以将光解反应产物与其热解产物进行比较。根据 PS-II 的 WOC 锰簇所需的分子组装，我们使用自旋载体亚氨基苯酚功能化配体，即 Lawsone Oxime（L-1）和 Phthiocol Oxime（L-2），有策略地合成了二聚体（M-1、M-2）、三聚体（M-3A、M-3B）和四聚体（M-4）。通过元素分析、热重分析、差热分析、粉末 X 射线衍射和红外光谱分析对这些配体进行了表征。通过氢键将各种氧化还原形式和立体异构形式的配体与分子结合的稳定能量与借助 Coats 和 Redfern 的升温关系计算出的配位聚合物将配体排出所需的热能进行了比较。结果发现，采用相同的合成路线，通过反离子在配位层中建立四聚体（M-4）和二聚体（M-2）所需的活化能相当（~37.48±1 kJ moL-1）。从 TG-DTA 数据中得到的氧化还原活性配体价态同系物的定量能量在生成模型化合物（即四聚体、二聚体的二聚体和三聚体）的过程中发挥了重要作用。根据氧化、乙酰和自旋载体配体的驱逐能，提出了它们在模型团簇化合物中的作用。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Mn: MVol.D5, 27.1.4.8, page 245 - 246
  作者：

  DOI：——

  日期：——
• Manganese(II) chelates of naturally occurring vitamin K artifacts
  作者：S.B. Padhye、S.Y. Rane、S.G. Gupta

  DOI：10.1016/0020-1650(78)80035-x

  日期：1978.1
• Anderson; Newman, Journal of Biological Chemistry, 1933, vol. 103, p. 405,409
  作者：Anderson、Newman

  DOI：——

  日期：——
• Thermal, spectral and magnetic properties of 2-hydroxy-1,4-naphthoquinone monoximates of Ho(III), Er(III) and Yb(III)
  作者：S. B. Jagtap、R. C. Chikate、O. S. Yemul、R. S. Ghadage、B. A. Kulkarni

  DOI：10.1023/b:jtan.0000042172.51676.7f

  日期：——

  Ho(III), Er(III) and Yb(III) complexes of 2-hydroxy-1,4-naphthoquinone-1-oxime derivatives having [ML3(H2O)(2)] are characterized using spectral and thermal decomposition studies. The thermolytic patterns suggested that they are decomposed in three distinct stages; 1(st) stage is related to the loss of two coordinated water molecules while one of the coordinated ligands and remaining two ligands are lost during subsequent 2(nd) and 3(rd) stages of degradation. After the 2(nd) stage, the structure of these complexes is reorganized reflecting that the structural associations through intermolecular hydrogen bonding network is essential for thermal stability. The kinetic parameters computed for 2(nd) step using the non-isothermal procedures of Coats - Redfern are applied to the respective differential thermogravimetric plots to ascertain the thermal degradation mechanism in air. The order of thermal decomposition reaction is found to be between 1 - 2 indicating that more than one intermediate might have simultaneously been formed. It also reveals the intermixing of 1(st) and 3(rd) stages of decomposition with the predominant 2(nd) stage leading to more gradual degradation. Energy of activation for 2(nd) stage of decomposition for these complexes is comparatively lower than those observed earlier for similar types of complexes. Other spectral data indicate oximino nitrogen and phenolato oxygen as coordination sites of 2-hydroxy-1,4-naphthoquinone monoximates.