ferrocenylmethylphosphonic acid | 385817-02-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: ferrocenylmethylphosphonic acid
• 英文别名: Fe(η(5)-C5H5)(η(5)-C5H4CH2PO(OH)2)；Dihydroxyphosphorylmethylferrocene；cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-ylmethylphosphonic acid;iron(2+)
• CAS: 385817-02-7
• 化学式: C₁₁H₁₃FeO₃P
• 分子量: 280.043
• InChiKey: KDNKPLUENIJBLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(triphenylphosphine)platinum(II) 、 二氯甲烷 、 ferrocenylmethylphosphonic acid 、 silver(l) oxide 以 二氯甲烷 为溶剂， 以86%的产率得到Fe(η(5)-C5H5)(η(5)-C5H4)CH2PO3Pt(P(C6H5)3)2*CH2Cl2
  参考文献：
  名称：

  Platinum(II) complexes containing ferrocene-derived phosphonate ligands; synthesis, structural characterisation and antitumour activity

  摘要：

  Platinum ferrocenyl-phosphonate complexes, containing four-membered Pt-O-P(O)-O rings, have been synthesised by the reactions Of CiS-[PtCl2(PPh3)(2)] with the ferrocene-derived phosphonic acids Fc(CH2)(n)P(O)(OH)(2) (n = 0-2) [Fc = (eta (5)-C5H4)Fe(eta (5)-C5H5)] and 1,1 ' -Fe ' [P(O)(OH)(2)](2) [Fc ' = Fe(eta (5)-C5H4)(2)] in the presence of A920. The complexes have been characterised by NMR spectroscopy, together with crystal structure determinations on [Fc(CH2)nPO(3)Pt(PPh3)(2)] (n = 1, 2) and [1,1 ' -Fc ' {PO3Pt(PPh3)(2)}(2)] The complexes [Fc(CH2)(n)PO3Pt(PPh3)(2)] (n = 1, 2) show moderate activity against P388 leukaemia cells, whereas the parent phosphonic acids are inactive. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(01)00584-9
• 作为产物：
  描述：

  diethyl (ferrocenylmethyl)phosphonate 在 trimethylbromosilane 、 aq. HCl 、 (C₂H₅)3N 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到ferrocenylmethylphosphonic acid
  参考文献：
  名称：

  Improved synthesis of diethyl ferrocenylphosphonate, crystal structure of (FcPO3Et2)2·ZnCl2, and electrochemistry of ferrocenylphosphonates, FcP(O)(OR)2, FcCH2P(O)(OR)2, 1,1′-fc[P(O)(OR)2]2 and [FcP(O)(OEt)2]2·ZnCl2 (Fc=(η5C5H5)Fe(η5C5H4), fc=(η5C5H4)Fe(η5C5H4), R=Et, H)

  摘要：

  An improved synthesis of diethyl ferrocenylphosphonate using the (BuLi)-Bu-t/(BuOK)-Bu-t system at low temperature is reported and the structure of [FcPO(3)Et(2)](2)(ZnCl2)-Zn-. complex is described. The electrochemical behaviour of FcP(O)(OEt)(2), 1,1'-fc[P(O)(OEt)(2)](2), FcCH(2)P(O)(OEt)(2), and their corresponding acids were compared. Each of them shows a reversible one-electron transfer reaction. Ferrocenylbisphosphonate is more difficult to oxidize than ferrocenylphosphonate due to the presence of two electron-withdrawing substituents. A methylene spacer between the ferrocenyl unit and the phosphonate group renders the compound easier to oxidize. The acids are easier to oxidize than the esters, and their salts, in which the phosphonate group behave as an electron-donating group, are even easier to oxidize than the ferrocene. The ferrocenylphosphonic acid may be, then, considered as a redox-active pH responsive molecule. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.05.031

文献信息

• Synthesis and characterisation of ferrocenyl-phosphonic and -arsonic acids
  作者：Steven R Alley、William Henderson

  DOI：10.1016/s0022-328x(01)00908-1

  日期：2001.12

  acids FcCH2CH2E(O)(OH)2 [4, E=P; 10, E=As; Fc=Fe(η5-C5H5)(η5-C5H4)] have been synthesized by the reaction of FcCH2CH2Br with either P(OEt)3 followed by hydrolysis, or with sodium arsenite followed by acidification. Reaction of FcCH2OH with (EtO)2P(O)Na gave FcP(O)(OEt)(OH), which was converted to FcCH2P(O)(OH)2 (3) by silyl ester hydrolysis using Me3SiBr–Et3N followed by aqueous work-up. Similarly, the

  二茂铁衍生的酸FcCH 2 CH 2 E（O）（OH）2 [ 4，E = P; 10，E ＝ As；FC =铁（η 5 -C 5 H ^ 5）（η 5 -C 5 H ^ 4）]通过FCCH的反应已被合成2 CH 2溴与任一P（OET）3，随后通过水解，或与亚砷酸钠，随后通过酸化。FcCH 2 OH与（EtO）2 P（O）Na的反应生成FCP（O）（OEt）（OH），将其转化为FcCH 2 P（O）（OH）2（3），使用Me 3 SiBr–Et 3 N进行甲硅烷基酯水解，然后进行水后处理。类似地，公知的膦酸FCP（O）（OH）2和新的衍生物1,1'--Fc的'[P（O）（OH）2 ] 2 [的Fc'=铁（η 5 -C 5 H ^ 4）2 ]和1,1'-Fc'[CH 2 P（O）（OH）2 ] 2（7）已通过其相应的酯合成。在3和7上进行了X射线晶体结构测定，并讨论了氢键网络。电喷雾质谱已用于各种酸的表征。膦酸可提供预期的[MH]