1-(2'-methylphenanthridinyl)-1,4,7,10-tetraazacyclododecane | 308821-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2'-methylphenanthridinyl)-1,4,7,10-tetraazacyclododecane
• 英文别名: 2-(1,4,7,10-Tetrazacyclododec-1-ylmethyl)phenanthridine；2-(1,4,7,10-tetrazacyclododec-1-ylmethyl)phenanthridine
• CAS: 308821-47-8
• 化学式: C₂₂H₂₉N₅
• 分子量: 363.506
• InChiKey: OWLMLZQGYYFFFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-((1S)-1-phenylethyl)acetamide 、 1-(2'-methylphenanthridinyl)-1,4,7,10-tetraazacyclododecane 在 caesium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以43%的产率得到(S,S,S)-1-(2'-methylphenanthridinyl)-4,7,10-tris[1-(1-phenyl)ethylcarbamoylmethyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission

  摘要：

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.

  DOI：

  10.1021/ja001797x
• 作为产物：
  描述：

  2-methylphenanthridine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 caesium carbonate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 2.25h， 生成 1-(2'-methylphenanthridinyl)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission

  摘要：

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.

  DOI：

  10.1021/ja001797x

文献信息

• The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission
  作者：James I. Bruce、Rachel S. Dickins、Linda J. Govenlock、Thorfinnur Gunnlaugsson、Stefan Lopinski、Mark P. Lowe、David Parker、Robert D. Peacock、Justin J. B. Perry、Silvio Aime、Mauro Botta

  DOI：10.1021/ja001797x

  日期：2000.10.1

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.