1-(3-phenylisoxazol-5-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine | 1546975-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-phenylisoxazol-5-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine
• 英文别名: N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1-pyridin-2-yl-N-(pyridin-2-ylmethyl)methanamine
• CAS: 1546975-40-9
• 化学式: C₂₂H₂₀N₄O
• 分子量: 356.427
• InChiKey: KFBRCCVDICKZFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-phenylisoxazol-5-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine 、 fac-[^99mTc(OH₂)₃(CO)₃](OSO₂CF₃) 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for fac-[M^I(CO)₃]⁺ Centers (M = Re, ^99mTc)

  摘要：

  Isoxazole ring formation was examined as a potential Cu-free alternative click reaction to Cu-I-catalyzed alkyne/azide cycloaddition. The isoxazole reaction was explored at macroscopic and radiotracer concentrations with the fac-[M-I(CO)(3)](+) (M = Re, Tc-99m) core for use as a noncoordinating linker strategy between covalently linked molecules. Two click assembly methods (click, then chelate and chelate, then click) were examined to determine the feasibility of isoxazole ring formation with either alkyne-functionalized tridentate chelates or their respective fac-[M-I(CO)(3)](+) complexes with a model nitrile oxide generator. Macroscale experiments, alkyne-functionalized chelates, or Re complexes indicate facile formation of the isoxazole ring. Tc-99m experiments demonstrate efficient radiolabeling with click, then chelate; however, the chelate, then click approach led to faster product formation, but lower yields compared to the Re analogues.

  DOI：

  10.1021/ic402825t
• 作为产物：
  描述：

  N,N-二(2-吡啶甲基)炔丙氨 、 benzohydroximoyl chloride 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以45%的产率得到1-(3-phenylisoxazol-5-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine
  参考文献：
  名称：

  Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for fac-[M^I(CO)₃]⁺ Centers (M = Re, ^99mTc)

  摘要：

  Isoxazole ring formation was examined as a potential Cu-free alternative click reaction to Cu-I-catalyzed alkyne/azide cycloaddition. The isoxazole reaction was explored at macroscopic and radiotracer concentrations with the fac-[M-I(CO)(3)](+) (M = Re, Tc-99m) core for use as a noncoordinating linker strategy between covalently linked molecules. Two click assembly methods (click, then chelate and chelate, then click) were examined to determine the feasibility of isoxazole ring formation with either alkyne-functionalized tridentate chelates or their respective fac-[M-I(CO)(3)](+) complexes with a model nitrile oxide generator. Macroscale experiments, alkyne-functionalized chelates, or Re complexes indicate facile formation of the isoxazole ring. Tc-99m experiments demonstrate efficient radiolabeling with click, then chelate; however, the chelate, then click approach led to faster product formation, but lower yields compared to the Re analogues.

  DOI：

  10.1021/ic402825t

文献信息

• Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for <i>fac</i>-[M^I(CO)₃]⁺ Centers (M = Re, ^99mTc)
  作者：Shalina C. Bottorff、Benjamin B. Kasten、Jelena Stojakovic、Adam L. Moore、Leonard R. MacGillivray、Paul D. Benny

  DOI：10.1021/ic402825t

  日期：2014.2.17

  Isoxazole ring formation was examined as a potential Cu-free alternative click reaction to Cu-I-catalyzed alkyne/azide cycloaddition. The isoxazole reaction was explored at macroscopic and radiotracer concentrations with the fac-[M-I(CO)(3)](+) (M = Re, Tc-99m) core for use as a noncoordinating linker strategy between covalently linked molecules. Two click assembly methods (click, then chelate and chelate, then click) were examined to determine the feasibility of isoxazole ring formation with either alkyne-functionalized tridentate chelates or their respective fac-[M-I(CO)(3)](+) complexes with a model nitrile oxide generator. Macroscale experiments, alkyne-functionalized chelates, or Re complexes indicate facile formation of the isoxazole ring. Tc-99m experiments demonstrate efficient radiolabeling with click, then chelate; however, the chelate, then click approach led to faster product formation, but lower yields compared to the Re analogues.