2-(4-(3-(1,1-difluoro-3-triisopropylsilylprop-2-ynyl)diaziridin-3-yl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole | 1179925-39-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-(3-(1,1-difluoro-3-triisopropylsilylprop-2-ynyl)diaziridin-3-yl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole
• CAS: 1179925-39-3
• 化学式: C₂₈H₃₉F₂N₃O₂S₂Si
• 分子量: 579.851
• InChiKey: WXQHJUVCHGNUCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  75.23
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(4-(3-(1,1-difluoro-3-triisopropylsilylprop-2-ynyl)diaziridin-3-yl)phenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.5h， 以97%的产率得到2-(4-(3-(1,1-difluoro-3-triisopropylsilylprop-2-ynyl)diazirin-3-yl)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
• 作为产物：
  描述：

  methyl 2,2-difluoro-4-(triisopropylsilyl)-3-butynoate 、 2-(4-iodophenylthio)-5-(4-methoxytetrahydropyran-4-yl)thiazole 在 正丁基锂 、 吡啶 、 盐酸羟胺 作用下， 以 四氢呋喃 、 正己烷 、 乙醇 为溶剂， 反应 4.0h， 以200 mg的产率得到2-(4-(3-(1,1-difluoro-3-triisopropylsilylprop-2-ynyl)diaziridin-3-yl)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