2,8-bis(1,3-dioxoisoindolin-2-yl)-10-(4-methoxyphenyl)-3,7-dimethylphenazine-10-ium 5-oxide-5-15N | 1361344-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,8-bis(1,3-dioxoisoindolin-2-yl)-10-(4-methoxyphenyl)-3,7-dimethylphenazine-10-ium 5-oxide-5-15N
• CAS: 1361344-11-7
• 化学式: C₃₇H₂₅N₄O₆
• 分子量: 622.622
• InChiKey: PLEJOBBAUAXDDL-XFVHPFTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  47.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  114.81
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,8-bis(1,3-dioxoisoindolin-2-yl)-10-(4-methoxyphenyl)-3,7-dimethylphenazine-10-ium 5-oxide-5-15N 在 sodium tetrahydroborate 、 sodium hydrogensulfite 、 sodium chloride 作用下， 以 异丙醇 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Manipulating reduction potentials in an artificial safranin cofactor

  摘要：

  Safranines hold great promise as artificial flavin-like electron transfer cofactors with tunable properties. We report the design and chemical synthesis of the p-methoxy derivative of safranine 0 using a new synthetic route based on the Ulmann condensation. Spectroelectrochemical comparison of the purified parent safranine and this derivative demonstrates that the modification increases its two-electron reduction potential by 125 mV, or 5.75 kcal/mol. This modification also causes redshifts in the absorbance and fluorescence spectra of the cofactor, suggesting that it may find future utility in arrayed sensor applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.028
• 作为产物：
  描述：

  2,2'-((4-methoxyphenylazanediyl)bis(2-methyl-5,1-phenylene))diisoindoline-1,3-dione 在 亚硝酸钠-15N 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以55%的产率得到2,8-bis(1,3-dioxoisoindolin-2-yl)-10-(4-methoxyphenyl)-3,7-dimethylphenazine-10-ium 5-oxide-5-15N
  参考文献：
  名称：

  Manipulating reduction potentials in an artificial safranin cofactor

  摘要：

  Safranines hold great promise as artificial flavin-like electron transfer cofactors with tunable properties. We report the design and chemical synthesis of the p-methoxy derivative of safranine 0 using a new synthetic route based on the Ulmann condensation. Spectroelectrochemical comparison of the purified parent safranine and this derivative demonstrates that the modification increases its two-electron reduction potential by 125 mV, or 5.75 kcal/mol. This modification also causes redshifts in the absorbance and fluorescence spectra of the cofactor, suggesting that it may find future utility in arrayed sensor applications. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.028