3-oxo-3-(2,4,5,7-tetramethoxynaphthalen-1-yl)propionic acid ethyl ester | 1335551-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-oxo-3-(2,4,5,7-tetramethoxynaphthalen-1-yl)propionic acid ethyl ester
• CAS: 1335551-15-9
• 化学式: C₁₉H₂₂O₇
• 分子量: 362.379
• InChiKey: VTVWHKLBOMZXTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-oxo-3-(2,4,5,7-tetramethoxynaphthalen-1-yl)propionic acid ethyl ester 在 盐酸 、 吡啶盐酸盐 作用下， 以 水 为溶剂， 反应 8.0h， 生成 3,4,6,7,9-pentahydroxyphenalen-1-one
  参考文献：
  名称：

  Synthesis of Tetrachalcogenide-Substituted Phenalenyl Derivatives: Preparation and Solid-State Characterization of Bis(3,4,6,7-tetrathioalkyl-phenalenyl)boron Radicals

  摘要：

  We report the synthesis and properties of a series of spiro-bis(3,4,6,7-tetrachalcogenide-substituted-phenalenyl)boron salts and two of the corresponding tetrathioalkyl-substituted spiro-bis(phenalenyl)boron radicals [tetrathiomethyl (10) and tetrathioethyl (11)] in which all of the active positions of the phenalenyl (PLY) nucleus are functionalized. In the solid state, radicals 10 and 11 exist as a weak pi-dimers due to the steric congestion of the thioalkyl groups in the superimposed PLY units. As a result, the spins are localized in the isolated (nonsuperimposed) PLY rings, and the structure, magnetic susceptibility measurements, and band structure calculations confirm that these PLY units are unable to undergo strong intermolecular interaction as a result of the orientation of the thioalkyl groups.

  DOI：

  10.1021/ja405814f
• 作为产物：
  描述：

  1,3,6,8-tetramethoxynaphthalene 、 氯甲酰乙酸乙酯 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 3-oxo-3-(2,4,5,7-tetramethoxynaphthalen-1-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Tetrachalcogenide-Substituted Phenalenyl Derivatives: Preparation and Solid-State Characterization of Bis(3,4,6,7-tetrathioalkyl-phenalenyl)boron Radicals

  摘要：

  We report the synthesis and properties of a series of spiro-bis(3,4,6,7-tetrachalcogenide-substituted-phenalenyl)boron salts and two of the corresponding tetrathioalkyl-substituted spiro-bis(phenalenyl)boron radicals [tetrathiomethyl (10) and tetrathioethyl (11)] in which all of the active positions of the phenalenyl (PLY) nucleus are functionalized. In the solid state, radicals 10 and 11 exist as a weak pi-dimers due to the steric congestion of the thioalkyl groups in the superimposed PLY units. As a result, the spins are localized in the isolated (nonsuperimposed) PLY rings, and the structure, magnetic susceptibility measurements, and band structure calculations confirm that these PLY units are unable to undergo strong intermolecular interaction as a result of the orientation of the thioalkyl groups.

  DOI：

  10.1021/ja405814f

文献信息

• 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.