(5-bromo-2-thienyl)(diphenyl)phosphine oxide | 1068163-11-0

• 分子结构分类: 有机化合物
• 英文名称: (5-bromo-2-thienyl)(diphenyl)phosphine oxide
• 英文别名: (5-bromothienyl)-2-diphenylphosphine oxide
• CAS: 1068163-11-0
• 化学式: C₁₆H₁₂BrOPS
• 分子量: 363.214
• InChiKey: TWPMTXCOZQFMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5-bromo-2-thienyl)(diphenyl)phosphine oxide 、 三丁基(2,3-二氢噻吩并[3,4-b]-[1,4]二恶英-5-基)锡烷 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以70%的产率得到(3',4'-ethylenedioxy-2',5-bithiophene)(diphenyl)phosphine oxide
  参考文献：
  名称：

  3D-conjugated systems based on oligothiophenes and phosphorus nodes

  摘要：

  我们合成了基于接枝在磷或氧化膦节点上的低聚噻吩片段的三维共轭体系。在 Stille 耦合条件下，溴端噻吩膦衍生物会发生磷碳键断裂，这归因于配体与钯催化剂的交换。紫外可见光谱、荧光光谱和循环伏安法分析了新化合物的电子特性。

  DOI：

  10.1039/b806169f
• 作为产物：
  描述：

  5-(diphenylphosphanyl)-2-bromothiophene 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以80%的产率得到(5-bromo-2-thienyl)(diphenyl)phosphine oxide
  参考文献：
  名称：

  3D-conjugated systems based on oligothiophenes and phosphorus nodes

  摘要：

  我们合成了基于接枝在磷或氧化膦节点上的低聚噻吩片段的三维共轭体系。在 Stille 耦合条件下，溴端噻吩膦衍生物会发生磷碳键断裂，这归因于配体与钯催化剂的交换。紫外可见光谱、荧光光谱和循环伏安法分析了新化合物的电子特性。

  DOI：

  10.1039/b806169f

文献信息

• Mn-Catalyzed Electrooxidative Undirected C–H/P–H Cross-Coupling between Aromatics and Diphenyl Phosphine Oxides
  作者：Siyuan Wang、Qilin Xue、Zhipeng Guan、Yayu Ye、Aiwen Lei

  DOI：10.1021/acscatal.1c00549

  日期：2021.4.2

  in C–P bond formation since it requires no pretreatment of substrates. Herein, we reported a Mn-catalyzed electrochemical intermolecular dehydrogenative cross-coupling between aryl C–H and diphenyl phosphine oxides. In undivided cells, a series of phosphorylation or diphosphorylation products could be obtained separately by adjusting the proportion of substrates. A catalytic amount of inexpensive Mn(II)

  C-P键广泛存在于许多生物活性化合物和功能分子中。过渡金属催化的脱氢C–H / P–H交叉偶联在C–P键的形成中起着至关重要的作用，因为它不需要对底物进行预处理。在本文中，我们报道了芳基CH和二苯基氧化膦之间Mn催化的电化学分子间脱氢交叉偶联。在未分裂的细胞中，可以通过调节底物的比例分别获得一系列的磷酸化或二磷酸化产物。使用了催化量的廉价Mn（II）盐，在此过程中不需要外部化学氧化剂。动力学同位素效应实验表明，CH活化不是决定速率的步骤。
• Synthesis of 1,1′,2-Trisubstituted Aryl-Based Ferrocenyl Phosphines as Precursors for Immobilized Ligands
  作者：Martyna Madalska、Peter Lönnecke、Vladimir Ivanovski、Evamarie Hey-Hawkins

  DOI：10.1021/om400449v

  日期：2013.10.28

  Ferrocenylaryl or ferrocenylheteroaryl phosphines bearing a carboxaldehyde group, [Fe1-PPh2(spacer)-2-NMe2CH2C3H3}(C5H4CHO)] (spacer = none (rac-12), 1,4-phenylene (rac-13), 1,3-phenylene (rac-14), 2,5-thienylene (rac-15)), were prepared in a facile four-step sequence starting with dibromination of N,N-dimethylaminomethylferrocene (1) followed by Negishi cross-coupling between 1,1'-dibromo-2-N,N-dimethylaminomethylferrocene (rac-2) and aryl or heteroaryl bromide phosphine oxides, Br-spacer-P(O)Ph-2 (spacer = 1,4-phenylene, 1,3-phenylene, 2,5-thienylene), reduction with trichlorosilane, and functionalization of the 1'-position of the cyclopentadienyl ring. All products were fully characterized by spectroscopy (H-1, C-13, and P-31 NMR, MS, IR) and for rac-3, rac-7 and rac-11 also by X-ray crystallography. Furthermore, preliminary studies on the grafting of rac-12 on silica were conducted.
• 1,2-Disubstituted Aryl-Based Ferrocenyl Phosphines
  作者：Martyna Madalska、Peter Lönnecke、Evamarie Hey-Hawkins

  DOI：10.1021/om400117n

  日期：2013.3.25

  Ferrocenylaryl- or ferrocenylheteroarylphosphines [Fe1-PPh2(spacer)-2-NMe2CH2C5H3}(C5H5)] (spacer = 1,4-phenylene (rac-6), 1,3-phenylene (rac-7), 4,4'-biphenylene (rac-8), 2,5-thienylene (rac-9)) were prepared in a facile two-step sequence starting with Negishi cross-coupling between N,N-dimethylaminomethylferrocene and aryl halide phosphine oxides, Br-spacer-P(O)Ph-2, by reduction with trichlorosilane. All products were characterized spectroscopically (H-1, C-13, and P-31 NMR, MS, FTIR), and rac-6, the corresponding phosphine oxide rac-2, and rac-9 were also characterized by X-ray crystallography. Furthermore, the redox properties of rac-2-9 were studied by cyclic voltammetry.