S-tridec-1-en-3-yl 2-diphenylphosphanylbenzenecarbothioate | 1244028-26-9

• 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: S-tridec-1-en-3-yl 2-diphenylphosphanylbenzenecarbothioate
• CAS: 1244028-26-9
• 化学式: C₃₂H₃₉OPS
• 分子量: 502.701
• InChiKey: ZARVLNIQWJILNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (2R)-3-nitrososulfanyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate 、 S-tridec-1-en-3-yl 2-diphenylphosphanylbenzenecarbothioate 以 乙腈 为溶剂， 反应 2.75h， 以71%的产率得到
  参考文献：
  名称：

  One-Pot Thioether Formation fromS-Nitrosothiols

  摘要：

  Protein S-nitrosation is an important post-translational modification. However, the detection of S-nitrosation is still problematic because S-nitrosation products, that is, S-nitrosothiols, are unstable species. Here a new reaction which can selectively convert unstable S-nitrosothiols to stable thioethers in one-pot under very mild conditions is reported. This reaction has the potential to be applied in the detection of protein S-nitrosation.

  DOI：

  10.1021/ol102491n
• 作为产物：
  描述：

  tridec-1-ene-3-thiol 、 2-二苯基膦苯甲酸 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 为溶剂， 以75%的产率得到S-tridec-1-en-3-yl 2-diphenylphosphanylbenzenecarbothioate
  参考文献：
  名称：

  还原连接介导的 S-亚硝基硫醇的一步二硫化物形成

  摘要：

  开发了一步还原连接介导的S-亚硝基硫醇的二硫化物形成。该反应涉及S-亚硝基与膦硫酯反应形成次磺酰胺和硫醇盐中间体，然后快速形成分子间二硫化物以形成稳定的缀合物。该反应可用于设计 S-亚硝化蛋白质的新型生物传感器。

  DOI：

  10.1021/ol101863s
• 作为试剂：
  描述：

  methyl (2R)-2-acetamido-3-(tridec-1-en-3-yldisulfanyl)propanoate 在 S-tridec-1-en-3-yl 2-diphenylphosphanylbenzenecarbothioate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到
  参考文献：
  名称：

  One-Pot Thioether Formation fromS-Nitrosothiols

  摘要：

  Protein S-nitrosation is an important post-translational modification. However, the detection of S-nitrosation is still problematic because S-nitrosation products, that is, S-nitrosothiols, are unstable species. Here a new reaction which can selectively convert unstable S-nitrosothiols to stable thioethers in one-pot under very mild conditions is reported. This reaction has the potential to be applied in the detection of protein S-nitrosation.

  DOI：

  10.1021/ol102491n

文献信息

• Reductive Ligation Mediated One-Step Disulfide Formation of <i>S</i>-Nitrosothiols
  作者：Jiming Zhang、Sheng Li、Dehui Zhang、Hua Wang、A. Richard Whorton、Ming Xian

  DOI：10.1021/ol101863s

  日期：2010.9.17

  reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

  开发了一步还原连接介导的S-亚硝基硫醇的二硫化物形成。该反应涉及S-亚硝基与膦硫酯反应形成次磺酰胺和硫醇盐中间体，然后快速形成分子间二硫化物以形成稳定的缀合物。该反应可用于设计 S-亚硝化蛋白质的新型生物传感器。
• One-Pot Thioether Formation from<i>S</i>-Nitrosothiols
  作者：Dehui Zhang、Nelmi O. Devarie-Baez、Jia Pan、Hua Wang、Ming Xian

  DOI：10.1021/ol102491n

  日期：2010.12.17

  Protein S-nitrosation is an important post-translational modification. However, the detection of S-nitrosation is still problematic because S-nitrosation products, that is, S-nitrosothiols, are unstable species. Here a new reaction which can selectively convert unstable S-nitrosothiols to stable thioethers in one-pot under very mild conditions is reported. This reaction has the potential to be applied in the detection of protein S-nitrosation.