2-(4-(2,2-difluoro-1-methoxy-2-[1-(2-{[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]amino}ethyl)-1H-1,2,3-triazol-4-yl]ethyl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole | 1179925-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 2-(4-(2,2-difluoro-1-methoxy-2-[1-(2-{[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]amino}ethyl)-1H-1,2,3-triazol-4-yl]ethyl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole
• CAS: 1179925-46-2
• 化学式: C₃₂H₄₁F₂N₇O₅S₃
• 分子量: 737.916
• InChiKey: WYFSOGJTURQXQQ-IOFCWMCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  141.52
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N-(2-azidoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide 、 2-(4-(2,2-difluoro-1-methoxybut-3-ynyl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole 在 copper(II) sulfate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以63%的产率得到2-(4-(2,2-difluoro-1-methoxy-2-[1-(2-{[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]amino}ethyl)-1H-1,2,3-triazol-4-yl]ethyl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole
  参考文献：
  名称：

  Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling

  摘要：

  A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochemically-induced coupling of a compound to its target followed by click reaction coupling with an azido-biotin reagent in order to facilitate purification of the labeled target. In a proof-of-concept study we have shown that 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group could be photolyzed to efficiently furnish the methanol adduct 23 and that the generated highly unstable carbene does not react with the neighboring acetylene moiety. A subsequent click reaction with the azido- biotin derivative 25 proceeded smoothly to give triazole 26. This chemical probe should thus be of unique value for facilitating identification of the molecular structure of the target of a bioactive compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.048