N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole | 328084-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole
• 英文别名: 1-methyl-4,5-diphenyl(213C,1,3-15N2)imidazole
• CAS: 328084-22-6
• 化学式: C₁₆H₁₄N₂
• 分子量: 237.276
• InChiKey: VDIRUWTYFVIERN-ZXFIOCTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole 在 2,9,16,23-tetra-t-butyl-29H,31H-phthalocyanine 、 氧气 作用下， 以 一氟三氯甲烷 、 丙酮 为溶剂， 生成 N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole 2,5-endoperoxide
  参考文献：
  名称：

  Synthesis of a 13C,15N labeled imidazole and characterization of the 2,5-endoperoxide and its decomposition

  摘要：

  A synthesis of C-13, N-15 labeled imidazoles was developed which allows the direct detection of a transient 2,5-endoperoxide at -100 degreesC. The endoperoxide was thoroughly characterized by H-1,C-13 and N-15 NMR. Upon warming, the endoperoxide decomposes via a series of transient intermediates to (CO2)-C-13 and 1,2-diphenyl-ethanediimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01731-7
• 作为产物：
  描述：

  N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole 2,5-endoperoxide 以 一氟三氯甲烷 、 丙酮 为溶剂， 生成 N-methyl-2-13C-1,3-15N-4,5-diphenylimidazole
  参考文献：
  名称：

  Synthesis of a 13C,15N labeled imidazole and characterization of the 2,5-endoperoxide and its decomposition

  摘要：

  A synthesis of C-13, N-15 labeled imidazoles was developed which allows the direct detection of a transient 2,5-endoperoxide at -100 degreesC. The endoperoxide was thoroughly characterized by H-1,C-13 and N-15 NMR. Upon warming, the endoperoxide decomposes via a series of transient intermediates to (CO2)-C-13 and 1,2-diphenyl-ethanediimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01731-7

文献信息

• Photosensitized Oxidation of ¹³C,¹⁵N-Labeled Imidazole Derivatives
  作者：Ping Kang、Christopher S. Foote

  DOI：10.1021/ja012253d

  日期：2002.8.1

  rearranges to a carbamate 9 by opening and reclosing the five-membered ring. 9 decomposes to CO(2) and benzil diimine. A labile NH in the imidazole is crucial for the decomposition of the initially formed endoperoxide, otherwise the endoperoxide decomposes to regenerate starting material. Many similarities exist between the photooxidations of imidazole and guanosine in organic solvent, suggesting that the two

  开发了在五元环的不同位置具有同位素标记的咪唑的有效合成。我们对同位素标记的咪唑衍生物的光敏氧化进行了详细的机理研究。在 2-H，N1-H 咪唑的光氧化中观察到了一种新产品 CO(2)，但在 2-取代的咪唑中没有观察到。CO(2) 的碳来源于咪唑的 2C。如 18O 实验所示，CO(2) 的两个氧原子主要来自一分子氧。在同位素标记的咪唑的光敏氧化过程中，通过低温 NMR 检测到瞬态中间体。在不同温度和时间下对 13C NMR 的定量分析将一种中间体的形成与另一种中间体的损失联系起来，从而允许建立瞬态中间体的完全分解途径。单线态氧与 4,5-二苯基咪唑通过 [4 + 2] 环加成反应形成 2,5-内过氧化物，加热后分解为氢过氧化物。一个途径中的氢过氧化物失水形成咪唑酮 7，后者水解为羟基咪唑-2-酮 11。在另一途径中，氢过氧化物重排为二醇 8。通过打开和重新关闭五-，二醇重排为氨基甲酸酯 9。成员环。9
• Synthesis of a 13C,15N labeled imidazole and characterization of the 2,5-endoperoxide and its decomposition
  作者：Ping Kang、Christopher S Foote

  DOI：10.1016/s0040-4039(00)01731-7

  日期：2000.12

  A synthesis of C-13, N-15 labeled imidazoles was developed which allows the direct detection of a transient 2,5-endoperoxide at -100 degreesC. The endoperoxide was thoroughly characterized by H-1,C-13 and N-15 NMR. Upon warming, the endoperoxide decomposes via a series of transient intermediates to (CO2)-C-13 and 1,2-diphenyl-ethanediimine. (C) 2000 Elsevier Science Ltd. All rights reserved.