3,3,6,6,10-Pentamethyl-3,4,6,10-tetrahydro-2H,7H-acridine-1,8-dione | 325966-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,6,6,10-Pentamethyl-3,4,6,10-tetrahydro-2H,7H-acridine-1,8-dione
• CAS: 325966-07-2
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: XCCOBOMETWDYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,3,6,6,10-Pentamethyl-3,4,6,10-tetrahydro-2H,7H-acridine-1,8-dione 在 高氯酸 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, Characterization, and Electrochemistry of Some Acridine-1,8-dione Dyes

  摘要：

  The synthesis, characterization, and electrochemical behavior of some acridinedione derivatives are reported. Cyclic voltammetric studies show that all the dyes undergo irreversible oxidation irrespective of the substitution on the nitrogen. The product formed on oxidation is the aromatic derivative in the case of N-H compounds and the acridinium salt in the case of the N-substituted compounds, which have been isolated and characterized. Formation of an intermediate carbon-centered radical is observed as evidenced by ESR spin-trapping experiments. A mechanistic scheme for the electrochemical oxidation is proposed. On carrying out reduction after oxidation, different products are formed depending on the substitution on the nitrogen. There is no reduction of the oxidized product in the case of N-H compounds, and compounds with substitution on nitrogen undergo reduction consistent with the observation in N-alkylpyridinium salts.

  DOI：

  10.1021/jo9600316
• 作为产物：
  描述：

  2-[(4,4-二甲基-2,6-二氧代环己基)甲基]-5,5-二甲基环己烷-1,3-二酮 在 氧气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 3,3,6,6,10-Pentamethyl-3,4,6,10-tetrahydro-2H,7H-acridine-1,8-dione
  参考文献：
  名称：

  Synthesis, Characterization, and Electrochemistry of Some Acridine-1,8-dione Dyes

  摘要：

  The synthesis, characterization, and electrochemical behavior of some acridinedione derivatives are reported. Cyclic voltammetric studies show that all the dyes undergo irreversible oxidation irrespective of the substitution on the nitrogen. The product formed on oxidation is the aromatic derivative in the case of N-H compounds and the acridinium salt in the case of the N-substituted compounds, which have been isolated and characterized. Formation of an intermediate carbon-centered radical is observed as evidenced by ESR spin-trapping experiments. A mechanistic scheme for the electrochemical oxidation is proposed. On carrying out reduction after oxidation, different products are formed depending on the substitution on the nitrogen. There is no reduction of the oxidized product in the case of N-H compounds, and compounds with substitution on nitrogen undergo reduction consistent with the observation in N-alkylpyridinium salts.

  DOI：

  10.1021/jo9600316

文献信息

• Photooxidation of acridine(1,8)dione dyes: flash photolysis investigation of the mechanistic details
  作者：N. Srividya、P. Ramamurthy、V. T. Ramakrishnan

  DOI：10.1039/b005502f

  日期：——

  Photolysis of the acridinedione dyes leads to the formation of different products depending on the substitutents. The cationic radical and the solvated electron are the primary photoproducts. Flash photolysis studies show that the solvated electron subsequently reacts with the ground state molecule to give the anion radical. The enolic form of the cation radical is also observed as an intermediate

  吖啶二酮染料的光解导致形成不同的产物，这取决于取代基。阳离子自由基和溶剂化电子是主要的光产物。闪光光解研究表明，溶剂化电子随后与基态分子反应生成阴离子自由基。还观察到阳离子自由基的烯醇形式作为中间体。阳离子自由基的阴离子自由基和烯醇形式分别在约 480 和 550 nm 处吸收。随后，这些自由基分别产生酮基和以碳为中心的自由基。以碳为中心的自由基在 650 nm 处吸收。