perfluorophenyl 3-methoxy-5-oxocyclohex-3-ene-1-carboxylate | 1122710-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: perfluorophenyl 3-methoxy-5-oxocyclohex-3-ene-1-carboxylate
• CAS: 1122710-49-9
• 化学式: C₁₄H₉F₅O₄
• 分子量: 336.215
• InChiKey: IBAKGFRRVMYBOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  perfluorophenyl 3-methoxy-5-oxocyclohex-3-ene-1-carboxylate 在 盐酸 、 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins

  摘要：

  We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modi. cations in the cell-cycle regulatory phosphatase Cdc25A. In addition, we show that DAz-1 has superior potency in cells compared to a biotinylated derivative. Collectively, these. findings set the stage for the development of activity-based inhibitors of Cdc25 cell-cycle phosphatases, which are sensitive to the redox state of the active-site cysteine and demonstrate the advantage of bioorthogonal conjugation methods to detect protein sulfenic acids in cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.073
• 作为产物：
  描述：

  3,5-二氧代环己烷羧酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 perfluorophenyl 3-methoxy-5-oxocyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins

  摘要：

  We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modi. cations in the cell-cycle regulatory phosphatase Cdc25A. In addition, we show that DAz-1 has superior potency in cells compared to a biotinylated derivative. Collectively, these. findings set the stage for the development of activity-based inhibitors of Cdc25 cell-cycle phosphatases, which are sensitive to the redox state of the active-site cysteine and demonstrate the advantage of bioorthogonal conjugation methods to detect protein sulfenic acids in cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.073