6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol | 1329634-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol
• 英文别名: 6-(4-methoxylphenylamino)-5,6-dihydro-1,10-phenanthroline；6-(4-Methoxyanilino)-5,6-dihydro-1,10-phenanthrolin-5-ol；6-(4-methoxyanilino)-5,6-dihydro-1,10-phenanthrolin-5-ol
• CAS: 1329634-86-7
• 化学式: C₁₉H₁₇N₃O₂
• 分子量: 319.363
• InChiKey: TXQRKRQRQIUHPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  67.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  水 、 sodium perchlorate monohydrate 、 cis-dichlorobis(1,10-phenanthroline)ruthenium(II) dihydrate 、 6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol 以 甲醇 、 水 为溶剂， 以60%的产率得到[Ru(1,10-phenanthroline)2(6-(4-methoxylphenylamino)-5,6-dihydro-1,10-phenanthroline)][ClO4]2*2H2O
  参考文献：
  名称：

  Epoxide ring opening in a zinc(II) complex in water without any Lewis acid catalyst: Formation of only one diastereomer out of 23

  摘要：

  The epoxide ring in 5,6-dihydro-5,6-epoxy-1,10-phenanthroline (L) opens up in its reaction with 4-methylaniline and 4-methoxyaniline in water in equimolar proportion at room temperature without any Lewis acid catalyst to give a monohydrate of 6-(4-methyl-phenylamino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L'center dot H2O) and 6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L '') respectively. Reaction time decreases from 72 to 14 h in boiling water. But the yields become less. Reaction of L with Zn(ClO4)(2)center dot 6H(2)O in methanol in 3:1 molar ratio at room temperature affords white [ZnL3](ClO4)(2)center dot H2O. The X-ray crystal structure of the acetonitrile solvate [ZnL3](ClO4)(2)center dot MeCN has been determined which shows that the metal has a distorted octahedral N-6 coordination sphere. [ZnL3](ClO4)(2)center dot 2H(2)O reacts with 4-methylaniline and 4-methoxyaniline in boiling water in 1:3 molar proportion in the absence of any Lewis acid catalyst to produce [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, respectively in 1-4 h time in somewhat low yield. In the H-1 NMR spectra of [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, only one sharp methyl signal is observed implicating that only one diastereomer out of the 2(3) possibilities is formed. The same diastereomers are obtained when L'center dot H2O and L '' are reacted directly with Zn(ClO4)(2)center dot 6H(2)O in tetrahydrofuran at room temperature in very good yields. Reactions of L'center dot H2O and L '' with Ru(phen)(2)Cl-2 center dot 2H(2)O (phen = 1,10-phenanthroline) in equimolar proportion in methanol-water mixture under refluxing condition lead to the isolation of two diastereomers of [Ru(phen)(2)L'](ClO4)(2)center dot 2H(2)O and [Ru(phen)(2)L ''](ClO4)(2)center dot 2H(2)O. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.04.037
• 作为产物：
  描述：

  甲氧苯胺 、 5,6-环氧-5,6-二氢-[1,10]菲咯啉 以 水 为溶剂， 反应 72.0h， 以70%的产率得到6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol
  参考文献：
  名称：

  Epoxide ring opening in a zinc(II) complex in water without any Lewis acid catalyst: Formation of only one diastereomer out of 23

  摘要：

  The epoxide ring in 5,6-dihydro-5,6-epoxy-1,10-phenanthroline (L) opens up in its reaction with 4-methylaniline and 4-methoxyaniline in water in equimolar proportion at room temperature without any Lewis acid catalyst to give a monohydrate of 6-(4-methyl-phenylamino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L'center dot H2O) and 6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L '') respectively. Reaction time decreases from 72 to 14 h in boiling water. But the yields become less. Reaction of L with Zn(ClO4)(2)center dot 6H(2)O in methanol in 3:1 molar ratio at room temperature affords white [ZnL3](ClO4)(2)center dot H2O. The X-ray crystal structure of the acetonitrile solvate [ZnL3](ClO4)(2)center dot MeCN has been determined which shows that the metal has a distorted octahedral N-6 coordination sphere. [ZnL3](ClO4)(2)center dot 2H(2)O reacts with 4-methylaniline and 4-methoxyaniline in boiling water in 1:3 molar proportion in the absence of any Lewis acid catalyst to produce [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, respectively in 1-4 h time in somewhat low yield. In the H-1 NMR spectra of [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, only one sharp methyl signal is observed implicating that only one diastereomer out of the 2(3) possibilities is formed. The same diastereomers are obtained when L'center dot H2O and L '' are reacted directly with Zn(ClO4)(2)center dot 6H(2)O in tetrahydrofuran at room temperature in very good yields. Reactions of L'center dot H2O and L '' with Ru(phen)(2)Cl-2 center dot 2H(2)O (phen = 1,10-phenanthroline) in equimolar proportion in methanol-water mixture under refluxing condition lead to the isolation of two diastereomers of [Ru(phen)(2)L'](ClO4)(2)center dot 2H(2)O and [Ru(phen)(2)L ''](ClO4)(2)center dot 2H(2)O. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.04.037

文献信息

• Epoxide ring opening in a zinc(II) complex in water without any Lewis acid catalyst: Formation of only one diastereomer out of 23
  作者：Nirmal K. Shee、F.A. Oluwafunmilayo Adekunle、Debashree Das、Michael G.B. Drew、Dipankar Datta

  DOI：10.1016/j.ica.2011.04.037

  日期：2011.9

  The epoxide ring in 5,6-dihydro-5,6-epoxy-1,10-phenanthroline (L) opens up in its reaction with 4-methylaniline and 4-methoxyaniline in water in equimolar proportion at room temperature without any Lewis acid catalyst to give a monohydrate of 6-(4-methyl-phenylamino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L'center dot H2O) and 6-(4-methoxyphenyl-amino)-5,6-dihydro-1,10-phenanthrolin-5-ol (L '') respectively. Reaction time decreases from 72 to 14 h in boiling water. But the yields become less. Reaction of L with Zn(ClO4)(2)center dot 6H(2)O in methanol in 3:1 molar ratio at room temperature affords white [ZnL3](ClO4)(2)center dot H2O. The X-ray crystal structure of the acetonitrile solvate [ZnL3](ClO4)(2)center dot MeCN has been determined which shows that the metal has a distorted octahedral N-6 coordination sphere. [ZnL3](ClO4)(2)center dot 2H(2)O reacts with 4-methylaniline and 4-methoxyaniline in boiling water in 1:3 molar proportion in the absence of any Lewis acid catalyst to produce [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, respectively in 1-4 h time in somewhat low yield. In the H-1 NMR spectra of [ZnL3'](ClO4)(2)center dot 4H(2)O and [ZnL3 ''](ClO4)(2)center dot H2O, only one sharp methyl signal is observed implicating that only one diastereomer out of the 2(3) possibilities is formed. The same diastereomers are obtained when L'center dot H2O and L '' are reacted directly with Zn(ClO4)(2)center dot 6H(2)O in tetrahydrofuran at room temperature in very good yields. Reactions of L'center dot H2O and L '' with Ru(phen)(2)Cl-2 center dot 2H(2)O (phen = 1,10-phenanthroline) in equimolar proportion in methanol-water mixture under refluxing condition lead to the isolation of two diastereomers of [Ru(phen)(2)L'](ClO4)(2)center dot 2H(2)O and [Ru(phen)(2)L ''](ClO4)(2)center dot 2H(2)O. (C) 2011 Elsevier B.V. All rights reserved.