2-diphenylphosphanyl benzoic acid 4-nitrophenyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2-diphenylphosphanyl benzoic acid 4-nitrophenyl ester
• 英文别名: (4-Nitrophenyl) 2-diphenylphosphanylbenzoate
• 化学式: C₂₅H₁₈NO₄P
• 分子量: 427.396
• InChiKey: QIVKNOSUMXEQQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苄基叠氮 、 2-diphenylphosphanyl benzoic acid 4-nitrophenyl ester 在 水 作用下， 以 氘代乙腈 为溶剂， 生成 diphenylphosphine oxide
  参考文献：
  名称：

  Mechanistic Investigation of the Staudinger Ligation

  摘要：

  The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. Hammett analyses demonstrated that electron-donating substituents on the phosphine accelerate the overall reaction. The electronic and steric properties of the ester had no significant impact on the overall rate but did affect product ratios. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. These findings establish a platform for optimizing the Staudinger ligation for expanded use in biological applications.

  DOI：

  10.1021/ja044461m
• 作为产物：
  描述：

  对硝基苯酚 、 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60%的产率得到2-diphenylphosphanyl benzoic acid 4-nitrophenyl ester
  参考文献：
  名称：

  Mechanistic Investigation of the Staudinger Ligation

  摘要：

  The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. Hammett analyses demonstrated that electron-donating substituents on the phosphine accelerate the overall reaction. The electronic and steric properties of the ester had no significant impact on the overall rate but did affect product ratios. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. These findings establish a platform for optimizing the Staudinger ligation for expanded use in biological applications.

  DOI：

  10.1021/ja044461m

文献信息

• FLUORESCENCE ASSAYS WITH IMPROVED SENSITIVITY
  申请人：RAINES Ronald T.

  公开号：US20090299061A1

  公开（公告）日：2009-12-03

  Latent fluorescent compounds, comprising a fluorescent molecule with one or more blocking groups attached and optionally one or more urea-containing groups are provided. The urea-containing group can be used to further attach one or more molecules of interest, such as proteins, peptides or nucleic acids. The blocking group(s) is released from the latent fluorescent compound by reaction with a trigger, forming the fluorescent molecule which can be detected. Also provided herein are methods of using latent fluorescent compounds to detect triggers.
• US7534902B2
  申请人：——

  公开号：US7534902B2

  公开（公告）日：2009-05-19
• US8034928B2
  申请人：——

  公开号：US8034928B2

  公开（公告）日：2011-10-11
• Mechanistic Investigation of the Staudinger Ligation
  作者：Fiona L. Lin、Helen M. Hoyt、Herman van Halbeek、Robert G. Bergman、Carolyn R. Bertozzi

  DOI：10.1021/ja044461m

  日期：2005.3.1

  The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. Hammett analyses demonstrated that electron-donating substituents on the phosphine accelerate the overall reaction. The electronic and steric properties of the ester had no significant impact on the overall rate but did affect product ratios. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. These findings establish a platform for optimizing the Staudinger ligation for expanded use in biological applications.