methyl rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylate | 867061-34-5

• 英文名称: methyl rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylate
• CAS: 867061-34-5
• 化学式: C₂₅H₂₃FeO₂P
• 分子量: 442.277
• InChiKey: IXYOZPVSXXWTMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 methyl rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylate 以 氯仿 为溶剂， 生成 dichloro-[methyl rac-2-[(diphenylphosphino-κP)methyl]ferrocenecarboxylate]-(η5-pentamethylcyclopentadienyl)rhodium(III)
  参考文献：
  名称：

  Synthesis and structural characterization of rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylic acid, its selected derivatives and some rhodium complexes

  摘要：

  rac-2-[(Diphenylphosphino)methyl]ferrocenecarboxylic acid (1) was prepared in a good yield from rac-2-(N,N-dimethylaminomethyl)bromoferrocene (2) via rac-2-(hydroxymethyl)bromoferrocene (4) and rac-2-[(diphenylphosphino)methyl]bromoferrocene (5), and further converted to the respective phosphine oxide (6), phosphine sulfide (7) and methyl ester (8). The phosphines 1 and 8 were studied as ligands in rhodium complexes. The reaction of di-mu-chloro-bis[chloro-(eta(5)-pentamethylcyclopentadienyl)rhodium(III)] with the stoichiometric amounts of 1 and 8 yielded the corresponding mononuclear complexes with P-monodentate ligands: [RhCl2,(eta(5)-C5Me5)(L-kappa P)], 9 and 10, respectively. Attempted deprotonation of 9 with LiBu or KOt-Bu gave intractable mixtures, in which the parent complex 9 as the major component was accompanied by two new compounds, likely the diastereoizomeric phosphinocarboxylate complexes. A defined O,P-chelating phosphinocarboxylate complex, [SP-4-2]-carbonyl-[rac-2-{(diphenylphosphino)methyl}ferrocenecarboxylato-kappa O-2,P]-tricyclohexylphosphinerhodium(I) (12), was obtained from the displacement of acetylacetonate(1-) (acac) ligand in [Rh(acac)(CO)(PCy3)] (Cy = cyclohexyl) with acid 1. The structures of 1, 6 - CHCl3, and 7 - 1/2CH(2)Cl(2), 10, and hydrated complexes 9 and 12 were determined by single-crystal X-ray diffraction. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.06.035
• 作为产物：
  描述：

  重氮甲烷 、 rac-2-[(diphenylphosphanyl)methyl]ferrocenecarboxylic acid 以 四氢呋喃 、 乙醚 为溶剂， 以98%的产率得到methyl rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylate
  参考文献：
  名称：

  Synthesis and structural characterization of rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylic acid, its selected derivatives and some rhodium complexes

  摘要：

  rac-2-[(Diphenylphosphino)methyl]ferrocenecarboxylic acid (1) was prepared in a good yield from rac-2-(N,N-dimethylaminomethyl)bromoferrocene (2) via rac-2-(hydroxymethyl)bromoferrocene (4) and rac-2-[(diphenylphosphino)methyl]bromoferrocene (5), and further converted to the respective phosphine oxide (6), phosphine sulfide (7) and methyl ester (8). The phosphines 1 and 8 were studied as ligands in rhodium complexes. The reaction of di-mu-chloro-bis[chloro-(eta(5)-pentamethylcyclopentadienyl)rhodium(III)] with the stoichiometric amounts of 1 and 8 yielded the corresponding mononuclear complexes with P-monodentate ligands: [RhCl2,(eta(5)-C5Me5)(L-kappa P)], 9 and 10, respectively. Attempted deprotonation of 9 with LiBu or KOt-Bu gave intractable mixtures, in which the parent complex 9 as the major component was accompanied by two new compounds, likely the diastereoizomeric phosphinocarboxylate complexes. A defined O,P-chelating phosphinocarboxylate complex, [SP-4-2]-carbonyl-[rac-2-{(diphenylphosphino)methyl}ferrocenecarboxylato-kappa O-2,P]-tricyclohexylphosphinerhodium(I) (12), was obtained from the displacement of acetylacetonate(1-) (acac) ligand in [Rh(acac)(CO)(PCy3)] (Cy = cyclohexyl) with acid 1. The structures of 1, 6 - CHCl3, and 7 - 1/2CH(2)Cl(2), 10, and hydrated complexes 9 and 12 were determined by single-crystal X-ray diffraction. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.06.035