2-diphenylphosphanyl benzoic acid 4-tolyl 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-tolyl ester
• 英文别名: (4-Methylphenyl) 2-diphenylphosphanylbenzoate
• 化学式: C₂₆H₂₁O₂P
• 分子量: 396.425
• InChiKey: PDCGOCPNQFWIEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苄基叠氮 、 2-diphenylphosphanyl benzoic acid 4-tolyl 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：

  对甲酚 、 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91%的产率得到2-diphenylphosphanyl benzoic acid 4-tolyl 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
• 作为试剂：
  描述：

  (Z)-2-乙酰氨基-3-苯基丙烯酸甲酯 在 [(cod)2Rh]BF₄ C₂₃H₁₇NO₃ 、 氢气 、 2-diphenylphosphanyl benzoic acid 4-tolyl ester 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 10.0h， 以5%的产率得到
  参考文献：
  名称：

  Self-assembled heteroleptic chiral ligands, assymetric catalyst systems and methods

  摘要：

  一种合成杂双核、含多金属的金属环催化剂的方法，特别适用于不对称催化，包括将多个含有多个功能基团的单齿配体以互补手性结合，所述多个功能基团通过连接体相互连接，在存在支架结构金属Ms或其衍生物的情况下，其中每个配体上至少一个功能基团结合以配位Msto形成双齿、以Ms为中心的配体支架，其中包含其余的功能基团，并将所述双齿配体支架与催化金属Mcor其衍生物结合，从而其余的功能基团结合以配位Mc，从而形成所述催化剂。

  公开号：

  US20060167294A1

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.
• US8034928B2
  申请人：——

  公开号：US8034928B2

  公开（公告）日：2011-10-11