3-Hydroxy-4,9-dimethoxyphenalen-1-on | 52588-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 3-Hydroxy-4,9-dimethoxyphenalen-1-on
• 英文别名: 3-Hydroxy-4,9-dimethoxyphenalen-1-one
• CAS: 52588-83-7
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: NGFIPLWHMXGOJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-4,9-dimethoxyphenalen-1-on 在 氢氧化钾 、 高氯酸 、 对甲苯磺酰叠氮 、 次氯酸叔丁酯 、 氢溴酸 、 维生素 C 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 49.67h， 生成 2,3,4,9-Tetrahydroxy-1-phenalenon
  参考文献：
  名称：

  Hofmann, Michael; Musso, Hans, Liebigs Annalen der Chemie, 1990, # 11, p. 1119 - 1124

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2,7-dimethoxy-1-naphthoylacetate 在 氢氟酸 作用下， 以83%的产率得到3-Hydroxy-4,9-dimethoxyphenalen-1-on
  参考文献：
  名称：

  1,3,4,9-Tetramethoxyphenalenyl system

  摘要：

  DOI：

  10.1021/jo00160a043

文献信息

• Naturally occurring compounds related to phenalenone. Part V. Synthetic approaches to structures based on 8,9-dihydro-8,8,9-trimethylphenaleno[1,2-b]furan-7-one
  作者：David A. Frost、George A. Morrison

  DOI：10.1039/p19730002159

  日期：——

  successful method involved acid-catalysed cyclisation of the keto-lactone (22)[2-(2,7-dimethoxy-1-naphthoyl)-3,3-dimethylpentan-4-olide]; another utilised the Claisen rearrangement of the dimethylallyl ether (24b)[9-hydroxy-4-methoxy-3-(3-methylbut-2-enyloxy)phenalenone].

  合成8,9-dihydro-8,8,9-trimethylphenaleno [1,2- b ]呋喃-7-one（21 b）及其1,6-二甲氧基-（21a）和1-的许多可能的合成途径已经研究了羟基-6-甲氧基-（21c）类似物。一种成功的方法涉及酸催化酮内酯（22）[2-（2,7-二甲氧基-1-萘甲酰基）-3,3-二甲基戊烷-4-内酯]的环化反应；另一个利用了二甲基烯丙基醚（24b）[9-羟基-4-甲氧基-3-（3-甲基丁-2-烯氧基）苯丙烯酮]的克莱森重排。
• Sulfur and selenium substituted spiro-biphenalenyl-boron neutral radicals
  作者：Arindam Sarkar、Sushanta K. Pal、Mikhail E. Itkis、Fook S. Tham、Robert C. Haddon

  DOI：10.1039/c2jm16001c

  日期：——

  We report a synthetic scheme for the preparation of alkylthio, dithio-bridged and diseleno-bridged 9-hydroxyphenalenones and associated spiro-biphenalenyl boron neutral radicals. We show that the strategy of sulfur substitution at the active positions of the phenalenyl units reduces the electrochemical disproportionation potential (ΔE2−1 = E2½ − E1½, where E1½ and E2½ are the first and second reduction potentials of corresponding cations) of the alkylthio-radicals [3,7-SR-PLY(O,O)]2B, (R = Me, 9), (R = Et, 10) and (R = Pr, 11), but brings about a significant reduction of the ΔE2−1 value in the case of disulfide and diselenide substitution, [3,4-S,S-PLY(O,O)]2B (12) and [3,4-Se,Se-PLY(O,O)]2B (13). The crystal structures of 10 and 11 show that the radicals exist as one dimensional (1-D) π-chains of superimposed phenalenyl units, and the molecular units pack more efficiently than the oxygen-substituted analog [3,7-OMe-PLY(O,O)]2B (8). Magnetic susceptibility measurements indicate that in the solid state the radicals remain paramagnetic while there is spin–spin interaction between the molecules along the π-chains. Band structure calculations are in accordance with the magnetic measurement data and indicate the presence of interactions between the molecules. The room temperature electrical conductivities of both compounds are found to be σRT = 1.5 × 10−2 S cm−1.

  我们报告了一种制备烷硫基、二硫基桥联和二硒基桥联的 9-羟基苯那烯酮以及相关的螺联苯那烯基硼中性基团的合成方案。我们表明，苯酚基单元活性位置的硫取代策略降低了烷硫基自由基的电化学歧化电位（ΔE2−1 = E2½ - E1½，其中E1½和E2½是相应阳离子的第一和第二还原电位） [3,7-SR-PLY(O,O)]2B、(R = Me, 9)、(R = Et, 10) 和 (R = Pr, 11)，但会显着降低 ΔE2−在二硫化物和二硒化物取代的情况下为 1 值，[3,4-S,S-PLY(O,O)]2B (12) 和 [3,4-Se,Se-PLY(O,O)]2B ( 13）。 10和11的晶体结构表明，自由基以叠加的苯酚单元的一维（1-D）π链形式存在，并且分子单元比氧取代的类似物[3,7-OMe-PLY（ O,O)]2B (8)。磁化率测量表明，在固态下，自由基保持顺磁性，同时沿着 π 链的分子之间存在自旋-自旋相互作用。能带结构计算与磁性测量数据一致，并表明分子之间存在相互作用。两种化合物的室温电导率为 σRT = 1.5 × 10−2 S cm−1。
• Hexathiophenalenylium Cations: Syntheses, Structures, and Redox Chemistry
  作者：Pradip Bag、Fook S. Tham、Bruno Donnadieu、Robert C. Haddon

  DOI：10.1021/ol400452f

  日期：2013.3.15

  Preparations of two hexathiophenalenylium compounds as stable salts from the reaction of 3,4,6,7-tetrathio-9-hydroxyphenalenone with Lawesson's reagent have been reported. The presence of three disulfide linkages on the periphery of the core phenalenyl unit is confirmed by X-ray crystallographic characterizations. Electrochemical cell potentials are lower than those of related dithio- and tetrathio-bridged phenalenyl radicals, and the hexathiophenalenyl radical shows a strong electron paramagnetic resonance (EPR) signal in the solid state.
• HADDON, R. C.;HIRANI, A. M.;KROLOFF, N. J.;MARSHALL, J. H., J. ORG. CHEM., 1983, 48, N 12, 2115-2117
  作者：HADDON, R. C.、HIRANI, A. M.、KROLOFF, N. J.、MARSHALL, J. H.

  DOI：——

  日期：——
• Tetrathiophenalenyl Radical and its Disulfide-Bridged Dimer
  作者：Leanne Beer、Robert W. Reed、Craig M. Robertson、Richard T. Oakley、Fook S. Tham、Robert C. Haddon

  DOI：10.1021/ol801159z

  日期：2008.7.17

  The presence of two disulfide groups in the tetrathiophenalenyl radical TTPLY leads to a highly delocalized spin distribution and the lowest cell potential ever observed for a monofunctional phenalenyl derivative. While the heteroatom substituents successfully block C-C bond formation, TTPLY nonetheless associates in the solid state to afford the hypervalent S-S-bonded dimer (TTPLY)(2).