pentachlorophenyl (E)-3-(4-(diethylphosphoryldifluoromethyl)phenyl)prop-2-enoate | 1175707-04-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: pentachlorophenyl (E)-3-(4-(diethylphosphoryldifluoromethyl)phenyl)prop-2-enoate
• CAS: 1175707-04-6
• 化学式: C₂₀H₁₆Cl₅F₂O₅P
• 分子量: 582.58
• InChiKey: NIYPCYNHIJYRAD-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  pentachlorophenyl (E)-3-(4-(diethylphosphoryldifluoromethyl)phenyl)prop-2-enoate 在 碘代三甲硅烷 、 2,2,2-三氟-N,N-二(三甲硅基)乙酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到pentachlorophenyl (E)-3-(4-(phosphoryldifluoromethyl)phenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3

  摘要：

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

  DOI：

  10.1021/ol9012662
• 作为产物：
  描述：

  (E)-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)acrylic acid 、 五氯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 以5.1 g的产率得到pentachlorophenyl (E)-3-(4-(diethylphosphoryldifluoromethyl)phenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3

  摘要：

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

  DOI：

  10.1021/ol9012662