(5-diphenylphosphine oxide)thienyl-2-N,N-dimethylaminomethylferrocene | 1427217-95-5

• 英文名称: (5-diphenylphosphine oxide)thienyl-2-N,N-dimethylaminomethylferrocene
• CAS: 1427217-95-5
• 化学式: C₂₉H₂₈FeNOPS
• 分子量: 525.434
• InChiKey: ITWACAICFNWUPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  (5-diphenylphosphine oxide)thienyl-2-N,N-dimethylaminomethylferrocene 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 以93%的产率得到(5-diphenylphosphino)thienyl-2-N,N-dimethylaminomethylferrocene
  参考文献：
  名称：

  1,2-Disubstituted Aryl-Based Ferrocenyl Phosphines

  摘要：

  Ferrocenylaryl- or ferrocenylheteroarylphosphines [Fe{1-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.

  DOI：

  10.1021/om400117n
• 作为产物：
  描述：

  N,N-dimethylaminomethylferrocene 、 (5-bromo-2-thienyl)(diphenyl)phosphine oxide 在 正丁基锂 、 zinc(II) chloride 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 以35%的产率得到(5-diphenylphosphine oxide)thienyl-2-N,N-dimethylaminomethylferrocene
  参考文献：
  名称：

  1,2-Disubstituted Aryl-Based Ferrocenyl Phosphines

  摘要：

  Ferrocenylaryl- or ferrocenylheteroarylphosphines [Fe{1-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.

  DOI：

  10.1021/om400117n

文献信息

• 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.