3-ferrocenylpropionic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-ferrocenylpropionic acid
• 英文别名: 3-ferrocenylpropanoic acid
• 化学式: C₁₃H₁₄FeO₂
• 分子量: 258.1
• InChiKey: AEHNINYHMFPCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ferrocenylpropionic acid 在 trifluoroacetic anhydride 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到[3]ferrocenophane-1-one
  参考文献：
  名称：

  N-Vinyl Ferrocenophane Pyrrole: Synthesis and Physical and Chemical Properties

  摘要：

  A new synthesis of [3]ferrocenophan-1-one has been developed, and a Trofimov reaction has been applied to its ketoxime. The novel subsequent N-vinyl pyrrole ferrocenophane displays reversible electrochemical behavior centered on the ferrocene, without any participation of the pyrrole. Unexpected byproduct was also isolated, in which the a-pyrrolic position is methylated.

  DOI：

  10.1021/om200839b
• 作为产物：
  描述：

  N,N-dimethylaminomethylferrocene 以 not given 为溶剂， 以24%的产率得到3-ferrocenylpropionic acid
  参考文献：
  名称：

  Linker effect of ferrocenylnaphthalene diimide ligands in the interaction with double stranded DNA

  摘要：

  Ferrocenylnaphthalene diimide ligands 1-7 were synthesized by joining a piperazino or N-methylamino linker of the naphthalene diimide skeleton with ferrocenecarboxylic, ferroceneacetic, or ferrocenepropionic parts. Their interaction with double stranded DNA (dsDNA) was studied kinetically and electrochemically. Association rate constants of these ligands were found to correlate with their intramolecular stacking ability between the ferrocene and naphthalene diimide planes: ligands which can adopt a stacked conformation in buffer solution were unfavorable in the association with dsDNA, resulting in a smaller association rate constant. Dissociation rate constants of these ligands carrying the bulky piperazino linker were smaller than that of those carrying an N-methylamino one. Binding constants were dictated by the balance of these two factors. These ligands were applied to the electrochemical detection of the amount of dsDNA on the electrode. Ligand 6 having the highest affinity for dsDNA gave rise to the largest current increase upon dsDNA formation in the electrochemical hybridization assay. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.01.011

文献信息

• Reduction of Escherichia coli ribonucleotide reductase subunit R2 with eight water-soluble ferrocene derivatives
  作者：Aimin Liu、David N. Leese、Jannie C. Swarts、A.Geoffrey Sykes

  DOI：10.1016/s0020-1693(02)01102-7

  日期：2002.9

  Abstract Water soluble ferrocenes [Fe(Cp)(CpL)], where Cp − is the η 5 -cyclopentadienide ligand and the side chain L is (a) the carboxylic acid group –(CH 2 ) x CO 2 H with x =0–4 ( I – V ); (b) the complex x =2 with the β-methylene mono-methyl substituted ( VI ); (c) the amine hydrochloride derivative with L=CH(Me) NH 3 + ( VII ); and (d) the complex with two Cp rings bridged by the amine hydrochloride

  摘要水溶性二茂铁[Fe（Cp）（CpL）]，其中Cp-为η5-环戊二烯配体，侧链L为（a）羧酸基团–（CH 2）x CO 2 H，x = 0 –4（I – V）；（b）被β-亚甲基单甲基取代的（VI）的络合物x ＝ 2；（c）具有L ＝ CH（Me）NH 3 +（VII）的胺盐酸盐衍生物；（d）具有两个被胺盐酸盐-CH（NH 3 +）CH 2 CH 2-（VIII）桥接的Cp环的配合物；已经制备了它们，并用作大肠杆菌核糖核苷酸还原酶的活性R2亚基的一当量还原剂。通过循环伏安法测定20 mM NaOH中酸I – VI的羧酸盐以及水中胺盐酸盐VII和VIII的形式还原电位E 1°'（25°C）与Nhe相比，我= 0.100 M（NaCl）。活性R2还原的二阶速率常数k 12（25°C）通过UV-Vis分光光度法测定，在I = 0.100 M时范围为0.15-0.50 M -1 s -1。 log
• A DFT-Elucidated Comparison of the Solution-Phase and SAM Electrochemical Properties of Short-Chain Mercaptoalkylferrocenes: Synthetic and Spectroscopic Aspects, and the Structure of Fc–CH₂CH₂–S–S–CH₂CH₂–Fc
  作者：Jan P. Lewtak、Marilé Landman、Israel Fernández、Jannie C. Swarts

  DOI：10.1021/acs.inorgchem.5b02936

  日期：2016.3.7

  mainly located on the sulfur. Rapid exothermic dimerization leads to the observed dimers, Fc(CH2)n–S–S–(CH 2)nFc. Reduction of the ferrocenium groups on the dimer occurs at potentials that still showed the ferrocenyl group ΔE = Epa,monomer – Epc,dimer ≤ 78 mV, indicating that the redox properties of the ferrocenyl group on the mercaptans are very similar to those of the dimer. 1H NMR measurements showed

  合成一系列难于获得的巯基烷基二茂铁即Fc（CH 2）n SH的简便合成方法，其中n = 1（1），2（2），3（3）或4（4）和Fc =铁（η 5 -C 5 H ^ 5）（η 5 -C 5 H ^ 4），被报告。在空气中观察到1 – 4二聚为相应的二硫化物19 – 22。在三斜空间群中结晶的二聚体20（Z = 2）P 1。二聚体20 - 22可以减少回原始的Fc（CH 2）Ñ SH衍生物与的LiAlH 4在回流的四氢呋喃中进行。密度泛函理论（DFT）计算表明，最高占据分子轨道1 - 4个位于完全放在二茂铁基暗示电化学氧化在约观察 -15 < E pa <76 mV（相对于FcH / FcH +）仅涉及Fe（II）到Fe（III）的过程。进一步的DFT计算表明，这种单电子氧化后，硫醇基上的质子损失，从而生成自由基Fc（CH 2）nS •，自旋密度主要位于硫上。快速放热二聚化导致观察到二聚体，即Fc（CH
• The influence of structure in the reaction of electrochemically generated ferrocenium derivatives with reduced glucose oxidase
  作者：Nigel J. Forrow、Gurdial S. Sanghera、Stephen J. Walters

  DOI：10.1039/b204702k

  日期：2002.8.8

  The synthesis and characterisation of a series of ferrocenylaminoalcohols is reported. 1,2-Aminoalcohol compounds were prepared from the respective ferrocene aldehydes via reaction with trimethylsilylcyanide followed by reduction with LiAlH4. This series includes the ferrocene derivative 1,1′-dimethyl-3-(2-amino-1-hydroxyethyl)ferrocene 1, which is used as a redox mediator to glucose oxidase in a commercial biosensor for determining blood glucose levels in diabetics. The aminoalcohol derivatives are included in a structure–activity study involving the electrochemical determination of the mediation rates of a range of systematically substituted ferrocenes with glucose oxidase. These mediation rates are correlated with structure.

  报道了一系列费罗烷基氨醇的合成与表征。1,2-氨醇化合物是通过与三甲基硅基氰化物反应，再用LiAlH4还原相应的费罗烷醛制备的。该系列包括费罗烷衍生物1,1'-二甲基-3-(2-氨基-1-羟基乙基)费罗烷1，该化合物被用作商业生物传感器中葡萄糖氧化酶的氧化还原介体，以测定糖尿病患者的血糖水平。这些氨醇衍生物被纳入了一项涉及系统性取代费罗烷与葡萄糖氧化酶的电化学介导速率结构-活性研究。这些介导速率与结构相关。
• RESIN COMPOSITION, OPTICAL FILTER, IMAGE DISPLAY DEVICE, SOLID-STATE IMAGING ELEMENT, AND COLORANT MIXTURE
  申请人：FUJIFILM Corporation

  公开号：US20210277249A1

  公开（公告）日：2021-09-09

  Provided are a resin composition including a colorant and a resin, in which the colorant contains two or more squarylium colorants represented by Formula (1) below, at least one of the squarylium colorants is a squarylium colorant having a hydrogen-bonding group, which is represented by Formula (2) below, and a colorant mixture consisting of the two or more squarylium colorants, which is included in the resin composition, has a maximum absorption wavelength in a wavelength range of 400 nm to 700 nm; an optical filter; a liquid crystal display device; a solid-state imaging element; and a colorant mixture.

  提供了一种树脂组合物，其中包括一种颜料和一种树脂，其中该颜料包含以下式（1）所代表的两种或两种以上的方三唑基颜料，其中至少一种方三唑基颜料是具有氢键结合基团的方三唑基颜料，其由以下式（2）表示，并且包含在树脂组合物中的两种或两种以上的方三唑基颜料的颜料混合物在波长范围为400纳米至700纳米的波长范围内具有最大吸收波长；光学滤光片；液晶显示装置；固态成像元件；以及颜料混合物。
• Ferrocene-Appended Cyclodextrins. The Effects of Temperature, Organic Solvent, Length of Spacer, and Cavity Size on the Complexation Behavior
  作者：Iwao Suzuki、Qiang Chen、Akihiko Ueno、Tetsuo Osa

  DOI：10.1246/bcsj.66.1472

  日期：1993.5

  Inclusion phenomena of cyclodextrins (CyDs) bearing a ferrocene moiety, 1—4, which have different cavity sizes and spacer lengths, were investigated by circular dichroism (CD) spectroscopy in pure ethylene glycol (EG) and 20% EG aqueous solution. β-CyD derivatives, 1 and 3, and a γ-CyD derivative, 4, form intramolecular complexes, including the ferrocene moiety in the CyD cavity with orientation similar to that in corresponding native CyD–ferrocene complexes, while another γ-CyD derivative, 2, which has no spacer alkyl chain, takes various conformations. The host–guest binding constants of 1—4 for several guests revealed that the ferrocene moiety of 1—4 depresses the guest binding, acting as an intramolecular inhibitor in guest binding. In particular, the depression was remarkable for 3 and 4 and the spacer alkyl chain was suggested to stabilize the intramolecular complexes. The ferrocene modified CyDs exhibit similar trends in guest selectivity to those of native CyDs. The effects of EG content on the binding constants of 1 and 2 revealed that hydrophobic effect operated in the guest accommodation. Thermodynamic parameters for the binding processes of 1 and 2 for 1-adamantanol were obtained from the temperature variations in binding constants, the values being −21.9 kJ mol−1 for ΔH° and 2.76 J mol−1 K−1 for ΔS° for 1 and −25.1 kJ mol−1 for ΔH° and −36.1 J mol−1 K−1 for ΔS° for 2. These values indicated that the complexation of 1 and 2 for 1-adamantanol was governed both by hydrophobic effect and van der Waals interaction, and the latter was especially important in the case of 1 and 1-adamantanol.

  在纯乙二醇（EG）和 20% EG 水溶液中，通过圆二色性光谱（CD）研究了含有二茂铁分子的环糊精（CyDs）1-4 的包合现象，这些环糊精具有不同的空腔尺寸和间隔长度。β-CyD衍生物1和3以及一种γ-CyD衍生物4形成了分子内配合物，包括CyD空腔中的二茂铁分子，其取向与相应的原生CyD-二茂铁配合物相似，而另一种没有间隔烷基链的γ-CyD衍生物2则呈现出各种构象。1-4 与几种客体的主-客体结合常数显示，1-4 的二茂铁分子抑制了客体的结合，在客体结合中起到了分子内抑制剂的作用。尤其是 3 和 4 的抑制作用更为明显，这表明间隔烷基链能稳定分子内复合物。二茂铁修饰的 CyDs 在客体选择性方面的趋势与原生 CyDs 相似。EG 含量对 1 和 2 结合常数的影响表明，疏水效应在客体容纳中起作用。根据结合常数的温度变化，得到了 1 和 2 与 1-金刚烷醇结合过程的热力学参数，其中 1 的 ΔH° 值为 -21.9 kJ mol-1，ΔS° 值为 2.76 J mol-1 K-1；2 的 ΔH° 值为 -25.1 kJ mol-1，ΔS° 值为 -36.1 J mol-1 K-1。这些数值表明，1-金刚烷醇与 1 和 2 的络合受疏水效应和范德华相互作用的影响，而后者在 1 和 1-金刚烷醇的络合中尤为重要。