N,N,N-(ferrocenylmethyl)trimethylammonium iodide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,N-(ferrocenylmethyl)trimethylammonium iodide
• 英文别名: (ferrocenylmethyl)trimethylammonium iodide；N,N-dimethylaminomethylferrocene methiodide；trimethyl(ferrocenylmethyl)ammonium iodide；trimethylaminomethylferrocene iodide；[FcCH₂NMe₃]I；Ferrocenylmethyltrimethylammonium iodide
• 化学式: C₁₄H₂₀FeN*I
• 分子量: 385.071
• InChiKey: YODDEGRGRRDRCF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N,N-(ferrocenylmethyl)trimethylammonium iodide 在 乌洛托品 作用下， 以 溶剂黄146 为溶剂， 以37%的产率得到二茂铁甲醛
  参考文献：
  名称：

  Bublitz, D. E.; Rinehart, K. L., 1969, vol. 17, p. 1 - 154

  摘要：

  DOI：
• 作为产物：
  描述：

  二茂铁甲醛 以 乙醚 为溶剂， 以76%的产率得到N,N,N-(ferrocenylmethyl)trimethylammonium iodide
  参考文献：
  名称：

  Some Acyl Ferrocenes and their Reactions

  摘要：

  DOI：

  10.1021/ja01570a027

文献信息

• Synthesis and reactivity of the ferrocene-derived phosphine [Fe(η-C5H5){η-C5H4CH2P(CH2OH)2}]
  作者：Nicholas J. Goodwin、William Henderson、Brian K. Nicholson、J. Kwabena Sarfo、John Fawcett、David R. Russell

  DOI：10.1039/a703666c

  日期：——

  The air-stable compound [Fe(η-C5H5)η-C5H4CH2P(CH2OH)2}] 1 has been prepared by the reaction of [Fe(η-C5H5)(η-C5H4CH2NMe3)]I with an excess of P(CH2OH)3. Compound 1 has been used to produce a range of other new compounds, thus demonstrating its versatility as a starting material; the phosphine oxide [Fe(η-C5H5)η-C5H4CH2P(O)(CH2OH)2}] 2, phosphine sulfide [Fe(η-C5H5)η-C5H4CH2P(S)(CH2OH)2}] 3, and other derivatives [Fe(η-C5H5)η-C5H4CH2P(CH2CH2CN)2}] 4, [Fe(η-C5H5)η-C5H4CH2P(CH2NEt2)2}] 5, [Fe(η-C5H5)η-C5H4CH2P(O)(CH2NEt2)2}] 6, [Fe(η-C5H5)η-C5H4CH2P(Me)(CH2OH)2}]I 7 and [Fe(η-C5H5)η-C5H4CH2P(Me)CH2OH}] 8. Crystal structure determinations for 1, 3 and 7 are reported and the hydrogen bonding of each structure described.

  空气稳定化合物 [Fe(η-C5H5)η-C5H4CH2P(CH2OH)2}] 1 通过 [Fe(η-C5H5)(η-C5H4CH2NMe3)]I 与过量 P(CH2OH)3 反应制备。化合物 1 已被用于合成一系列其他新化合物，从而展示了其作为起始材料的多样性；包括膦氧化物 [Fe(η-C5H5)η-C5H4CH2P(O)(CH2OH)2}] 2，膦硫化物 [Fe(η-C5H5)η-C5H4CH2P(S)(CH2OH)2}] 3，以及其他衍生物 [Fe(η-C5H5)η-C5H4CH2P(CH2CH2CN)2}] 4，[Fe(η-C5H5)η-C5H4CH2P(CH2NEt2)2}] 5，[Fe(η-C5H5)η-C5H4CH2P(O)(CH2NEt2)2}] 6，[Fe(η-C5H5)η-C5H4CH2P(Me)(CH2OH)2}]I 7 和 [Fe(η-C5H5)η-C5H4CH2P(Me)CH2OH}] 8。报道了 1、3 和 7 的晶体结构测定，并描述了每种结构的氢键。
• Synthesis of water soluble O-glycosides of N-(hydroxyalkyl)aminomethylferrocenes †
  作者：John S. Landells、Joy L. Kerr、David S. Larsen、Brian H. Robinson、Jim Simpson

  DOI：10.1039/a908512b

  日期：——

  -, [N-5-(β-D-glucopyranosyloxy)pentyl-N-methylaminomethyl]ferrocene, has been synthesized from the methiodide salt of N,N-dimethylaminomethylferrocene and N-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy-ethyl, -propyl and -pentyl)amine respectively. N-Methylation of the products from the latter reaction was achieved by formylation followed by reduction with lithium aluminium hydride. Catalytic hydrogenolysis

  一系列 水 可溶性二茂铁胺葡萄糖缀合物，[ N -2-（β- D-吡喃葡萄糖基氧基）乙基-，[ N -3-（β- D-吡喃葡萄糖基氧基）丙基-，[ N -5-（β- D-吡喃葡萄糖基氧基）戊基-N-甲基氨基甲基]二茂铁是分别由N，N-二甲基氨基甲基二茂铁和N-（3,4,6-三-O-苄基-β - D-吡喃葡糖基氧基-乙基，-丙基和-戊基）胺的甲硫醇盐合成的。N-甲基化 后一反应的产物通过 甲酰化 其次是 减少 和 氢化铝锂。钯催化氢解去除了苄基保护基团免受碳水化合物部分的影响，得到目标缀合物。使用三氟化硼的另一种[ N -2-（β- D-吡喃葡萄糖基氧基乙基）氨基甲基]二茂铁的合成方法–乙醚 晋升 糖基化 的 五-O-乙酰基-D-吡喃葡萄糖和[ N-（2-羟乙基）-N-甲基氨基甲基]二茂铁，然后脱乙酰还开发了使用碱性离子交换树脂的碳水化合物保护基。确定了水溶性缀合物的p K a值。
• Mössbauer Studies on Ferrocene Complexes
  作者：G. Neshvad、R.M.G. Roberts、J. Silver

  DOI：10.1016/s0022-328x(00)81032-3

  日期：1981.11

  Mössbauer and NMR spectra are reported for ferrocenyl (Fc) carbenium ions, FcCH2+(III+) and FcC+Me2(II+) in frozen acidic media. 1H-NMR spectra showed no evidence of FeH bonded species. Mössbauer parameters for II+ were identical within experimental error to those obtained for the carbenium ion precursors and to ferrocene itself, whereas quadrupole splittings for III+ were significantly larger. The

  报告了在冷冻酸性介质中二茂铁基（Fc）碳正离子，FcCH 2 +（III +）和FcC + Me 2（II +）的Mössbauer和NMR光谱。1 H-NMR光谱没有显示FeH键合物质的证据。在实验误差范围内，II +的Mössbauer参数与碳正离子前体和二茂铁本身的参数相同，而III +的四极分裂明显更大。后一种物质的结果通过与中心铁原子的轨道重叠的稳定化来解释。
• Highly efficient reduction of ferrocenyl derivatives by borane
  作者：Lucie Routaboul、Jérôme Chiffre、Gilbert G.A. Balavoine、Jean-Claude Daran、Eric Manoury

  DOI：10.1016/s0022-328x(01)00936-6

  日期：2001.12

  Borane, as a DMS or a THF complex, can efficiently reduce a large range of ferrocenyl derivatives (aldehydes, ketones, ethers, acetals, carboxylic acids, esters,…) if they bear at least one oxygen at a carbon at the α position. On the contrary, similar molecules, which contain nitrogen instead of oxygen, do not react with borane.

  硼烷作为DMS或THF络合物，如果它们在α位置的碳原子上带有至少一个氧，则可以有效地还原各种二茂铁基衍生物（醛，酮，醚，缩醛，羧酸，酯等）。相反，含有氮而不是氧的相似分子不会与硼烷反应。
• Copper complexes with ferrocenyl pendants: Evidence for an FeII ∼ CuII ⇌ FeIII ∼ CuI electron transfer equilibrium leading to a reaction with dioxygen
  作者：Andrew J. Evans、Scott E. Watkins、Donald C. Craig、Stephen B. Colbran

  DOI：10.1039/b105150b

  日期：2002.3.8

  Three new nitrogen-donor ligands with ferrocenyl pendants, namely ferrocenylmethylbis(2-pyridylethyl)amine (L1), ferrocenylmethylbis(2-pyridylmethyl)amine (L2), and 1-ferrocenylmethyl-4,7-diisopropyl-1,4,7-triazacyclononane (L3), have been synthesised. Copper(II) complexes of these ligands have been made and their physicochemical and redox properties characterised. Crystal structures of [Cu(L2)X2·0.5Et2O (X = Cl, Br), [Cu(L2)(OTf)2(CH3OH)], [Cu(L3)Cl2], and [(L3)Cu}2(μ-OH)2](OTf)2·0.5Et2O are reported. Oxidation of each complex with ceric ion affords the corresponding FeIII ∼ CuII species. Variations in ligand design, the choice of co-ligand (chloride, bromide, trifluoromethanesulfonate (OTf) or solvent) and the choice of solvent allowed, in the case of acetonitrile solutions of [Cu(L1)(H2O)2](OTf)2, the close matching of the FeIII–FeII and CuII–CuI electrochemical couples. [Cu(L1)(H2O)2](OTf)2 reacts with dioxygen in acetonitrile, but is stable in other solvents such as tetrahydrofuran. Electronic spectra of the complex in acetonitrile exhibit a prominent ferrocenium ion band. These results are interpreted in terms of an intramolecular electron transfer equilibrium between FeII ∼ CuII and FeIII ∼ CuI tautomers for the complex that leads to it reacting with dioxygen; their possible biological relevance is discussed.

  合成了三种具有二茂铁基配体的氮供体型配体，即二茂铁基甲基双(2-吡啶乙基)胺(L1)、二茂铁基甲基双(2-吡啶甲基)胺(L2)和1-二茂铁基甲基-4,7-二异丙基-1,4,7-三氮杂环壬烷(L3)。这些配体的铜(II)配合物被制备并表征了它们的物化性质和氧化还原性质。报道了[Cu(L2)X2·0.5Et2O (X = Cl, Br)、[Cu(L2)(OTf)2(CH3OH)]、[Cu(L3)Cl2]和[(L3)Cu}2(μ-OH)2](OTf)2·0.5Et2O的晶体结构。用铈离子氧化每个配合物会得到相应的FeIII≈CuII物种。配体设计的变体、配体的选择(氯化物、溴化物、三氟甲磺酸盐(OTf)或溶剂)和溶剂的选择使得[Cu(L1)(H2O)2](OTf)2的乙腈溶液的FeIII-FeII和CuII-CuI电化学耦合能够紧密匹配。[Cu(L1)(H2O)2](OTf)2在乙腈中与氧气反应，但在四氢呋喃等其他溶剂中稳定。该配合物在乙腈的电子光谱显示出明显的二茂铁离子带。这些结果被解释为配合物中FeII≈CuII与FeIII≈CuI异构体之间的分子内电子转移平衡，导致其与氧气反应;并讨论了它们可能的生物学相关性。