(pyridine-3-ylmethyl)diphenylphosphine oxide | 13119-81-8

• 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: (pyridine-3-ylmethyl)diphenylphosphine oxide
• 英文别名: Diphenyl-3-pyridylmethylphosphine oxide；-diphenylphosphinoxid；3-<(Diphenyl-phosphoryl)-methyl>-pyridin；3-[(Diphenyl-phosphoryl)-methyl]-pyridin；3-(Diphenylphosphorylmethyl)pyridine
• CAS: 13119-81-8
• 化学式: C₁₈H₁₆NOP
• 分子量: 293.305
• InChiKey: ZHGWFCNILYXKSE-UHFFFAOYSA-N

物化性质

• 沸点：
  445.1±28.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ω-(anthracene-9-yl)ethanal 、 (pyridine-3-ylmethyl)diphenylphosphine oxide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 以49%的产率得到3-<3-(9-Anthryl)propenyl>pyridine
  参考文献：
  名称：

  Intramolecular Charge Separation and Transition State Dynamics in Anthracene/Pyridinium Supermolecules

  摘要：

  The excited state dynamics of anthracene (donor) and pyridinium or pyridine (acceptor) composed supermolecules has been studied applying femtosecond transient absorption and picosecond time-resolved fluorescence techniques. From the analysis of spectral and temporal dynamics of sigma- and pi-bridged systems 1a-4a, the effects of molecular structure and environment on intramolecular charge separation in the excited state are differentiated. Two-step charge separation has been verified to occur for 2a and 3a in liquid environment by identifying neutral and radical ion states of the anthracene moiety on the sub picosecond time scale. Instead, after changing the substitution position of the acceptor to 3-pyridinium, charge separation does not occur. From evaluating the transient state dynamics in solvents of different polarity, rates for charge separation and relaxation can be quantified in terms of Marcus theory.

  DOI：

  10.1021/jp963967r
• 作为产物：
  描述：

  3-氯甲基吡啶盐酸盐 、 Diphenylphosphine oxide 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以87 %的产率得到(pyridine-3-ylmethyl)diphenylphosphine oxide
  参考文献：
  名称：

  来自红磷和官能化吡啶、咪唑、吡唑的磷化氢及其衍生物及其抗菌和细胞生长抑制活性

  摘要：

  通过元素磷或仲氧化膦与功能性吡啶、咪唑和吡唑的反应合成了含有吡啶、咪唑和吡唑基团的叔氧化膦、硫化膦和硒化膦。烷基三(2-吡啶基乙基)磷碘化物和溴化物也可通过相应膦的季铵化获得。评估了合成化合物（包括含氮杂环化合物、磷、硒和硫）对耐肠球菌、枯草芽孢杆菌、大肠杆菌、铜绿假单胞菌微生物的抗菌活性。发现带有咪唑 ( 14 , 19 ) 、吡唑 ( 13 ) 和吡啶片段 (5, 9 ) 和鏻盐 ( 11, 12 ) 可以被认为是新的有前途的抗菌剂。对于一些合成的化合物，LC 50是确定的。具有甲基吡唑片段 ( 13 ) 和磷盐 ( 11, 12 ) 的氧化膦显示出很强的抗菌活性，具有长链基团 ( 12 ) 的溴化磷的细胞毒性作用比顺铂高一个数量级。我们相信，所获得的结果可能有助于开发治疗和预防细菌感染和癌症的高效药物。

  DOI：

  10.1016/j.bioorg.2023.106363

文献信息

• Palladium-Catalyzed α-Arylation of Benzylic Phosphine Oxides
  作者：Sonia Montel、Tiezheng Jia、Patrick J. Walsh

  DOI：10.1021/ol403124g

  日期：2014.1.3

  A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)(2)/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).
• Intramolecular Charge Separation and Transition State Dynamics in Anthracene/Pyridinium Supermolecules
  作者：T. Hirsch、H. Port、H. C. Wolf、B. Miehlich、F. Effenberger

  DOI：10.1021/jp963967r

  日期：1997.6.1

  The excited state dynamics of anthracene (donor) and pyridinium or pyridine (acceptor) composed supermolecules has been studied applying femtosecond transient absorption and picosecond time-resolved fluorescence techniques. From the analysis of spectral and temporal dynamics of sigma- and pi-bridged systems 1a-4a, the effects of molecular structure and environment on intramolecular charge separation in the excited state are differentiated. Two-step charge separation has been verified to occur for 2a and 3a in liquid environment by identifying neutral and radical ion states of the anthracene moiety on the sub picosecond time scale. Instead, after changing the substitution position of the acceptor to 3-pyridinium, charge separation does not occur. From evaluating the transient state dynamics in solvents of different polarity, rates for charge separation and relaxation can be quantified in terms of Marcus theory.