2,2'-bis<5-dimethylamino-2-(p-dimethylaminophenyl)indan-1,3-dione> | 116341-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2'-bis<5-dimethylamino-2-(p-dimethylaminophenyl)indan-1,3-dione>
• 英文别名: 5-(dimethylamino)-2-[5-(dimethylamino)-2-[4-(dimethylamino)phenyl]-1,3-dioxoinden-2-yl]-2-[4-(dimethylamino)phenyl]indene-1,3-dione
• CAS: 116341-92-5
• 化学式: C₃₈H₃₈N₄O₄
• 分子量: 614.744
• InChiKey: FBLCOAMXNRGBOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'-bis<5-dimethylamino-2-(p-dimethylaminophenyl)indan-1,3-dione> 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Influence of onium substituent in phthaloyl ring on thermodynamic parameters of equilibrium between dimer and free radicals of 2-(4-dimethylaminophenyl)-1,3-indandiones

  摘要：

  2,2'-Bis[2-(4-dimethylaminophenyl)-5-trimethylammonio-1,3-indandione] diperchlorate and 2,2'-bis[2-(4-dimethylaminophenyl)-5-(2,4,6-triphenylpyridinio)-1,3-indandione] diperchlorate have very definite thermochromic and mechanochromic properties, owing to reversible dissociation into free radicals. The rupture energy of the central bond C2-C2' in 5-substituted 2,2'-bis[2-(4-dimethylaminophenyl)-1,3-indandiones] in acetonitrile is 63-75 kJ/mole; in the dimer with the bulky 5-(2,4,6-triphenylpyridinium) substituent, the rupture energy is 51 kJ/mole. The equilibrium constants follow the Hammett equation (rho = 1.53, acetonitrile, 293 K). Radicals with onium substituents are thermodynamically the most stable of the arylindandionyl radicals that are thus far known, owing to the significant contribution of electrostatic interactions.

  DOI：

  10.1007/bf00957842
• 作为产物：
  描述：

  5-dimethylamino-2-(p-dimethylaminophenyl)indan-1,3-dione 在 碘 、 sodium methylate 作用下， 反应 1.5h， 生成 2,2'-bis<5-dimethylamino-2-(p-dimethylaminophenyl)indan-1,3-dione>
  参考文献：
  名称：

  Dieckmann-Shapiro condensation of substituted phthalides with p-dimethylaminobenzaldehyde

  摘要：

  DOI：

  10.1007/bf00954613

文献信息

• NIKULIN V. I.; PISARENKO L. M., IZV. AN CCCP. CEP. XIM.,(1986) N 8, 1880-1855
  作者：NIKULIN V. I.、 PISARENKO L. M.

  DOI：——

  日期：——
• Thermodynamic parameters of free radical-dimer equilibria in phenylindandione derivatives
  作者：L. M. Pisarenko、V. I. Nikulin、A. B. Gagarina

  DOI：10.1007/bf00961905

  日期：1988.6
• Kinetics of the reversible recombination of substituted 2-(p-dimethylaminophenyl)indane-1,3-dion-2-yl radicals
  作者：L. M. Pisarenko、V. I. Nikulin、I. V. Khudyakov

  DOI：10.1007/bf00961092

  日期：1988.8
• Mechanochromatic effect and the formation of free radicals in bis(phenylphthaloyl)ethane dimers upon mechanical destruction in the solid phase
  作者：L. M. Pisarenko、A. B. Gagarina、V. A. Roginskii

  DOI：10.1007/bf00957263

  日期：1987.12