(2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 3-fluoro-4-hydrazinylbenzenesulfonate | 1335107-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 3-fluoro-4-hydrazinylbenzenesulfonate
• CAS: 1335107-41-9
• 化学式: C₁₄H₂₁FN₂O₅S
• 分子量: 348.396
• InChiKey: BJFXKRRJFFNIPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.88
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 3-fluoro-4-hydrazinylbenzenesulfonate 、 4-(3-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)prop-2-enoyl)benzonitrile 在 吡啶 、 4-甲基苯磺酸吡啶 作用下， 反应 38.0h， 以36%的产率得到(2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 4-(3-(4-cyanophenyl)-5-(4-(3,3,13,13-tetramethyl-2,4,12,14-tetraoxa-8,17,23-trithia-20-azadispiro[5.3.5.9]tetracosan-20-yl)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-3-fluorobenzene-1-sulfonate
  参考文献：
  名称：

  Designed To Dissolve: Suppression of Colloidal Aggregation of Cu(I)-Selective Fluorescent Probes in Aqueous Buffer and In-Gel Detection of a Metallochaperone

  摘要：

  Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem, we have developed a hydrophilic triarylpyrazoline-based fluorescent probe, CTAP-2, that dissolves directly in water and shows a rapid, reversible, and highly selective 65-fold fluorescence turn-on response to Cu(I) in aqueous solution. CTAP-2 proved to be sufficiently sensitive for direct in-gel detection of Cu(I) bound to the metallochaperone Atoxl, demonstrating the potential for cation-selective fluorescent probes to serve as tools in metalloproteomics for identifying proteins with readily accessible metal-binding sites.

  DOI：

  10.1021/ja207004v
• 作为产物：
  描述：

  (2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 3,4-difluorobenzenesulfonate 在 一水合肼 作用下， 以 二甲基亚砜 为溶剂， 以95%的产率得到(2,2,5-trimethyl-1,3-dioxan-5-yl)methyl 3-fluoro-4-hydrazinylbenzenesulfonate
  参考文献：
  名称：

  Designed To Dissolve: Suppression of Colloidal Aggregation of Cu(I)-Selective Fluorescent Probes in Aqueous Buffer and In-Gel Detection of a Metallochaperone

  摘要：

  Due to the lipophilicity of the metal-ion receptor, previously reported Cu(I)-selective fluorescent probes form colloidal aggregates, as revealed by dynamic light scattering. To address this problem, we have developed a hydrophilic triarylpyrazoline-based fluorescent probe, CTAP-2, that dissolves directly in water and shows a rapid, reversible, and highly selective 65-fold fluorescence turn-on response to Cu(I) in aqueous solution. CTAP-2 proved to be sufficiently sensitive for direct in-gel detection of Cu(I) bound to the metallochaperone Atoxl, demonstrating the potential for cation-selective fluorescent probes to serve as tools in metalloproteomics for identifying proteins with readily accessible metal-binding sites.

  DOI：

  10.1021/ja207004v