1,1'-bis[(2-propyn-1-yloxy)methyl]ferrocene | 1226860-94-1

• 英文名称: 1,1'-bis[(2-propyn-1-yloxy)methyl]ferrocene
• 英文别名: [Fc(CH2OCH2C.ident.CH)2]
• CAS: 1226860-94-1
• 化学式: C₁₈H₁₈FeO₂
• 分子量: 322.187
• InChiKey: KJFZOGUNGYWFQT-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：

  ethyl [(azidoacetyl)amino]acetate 、 1,1'-bis[(2-propyn-1-yloxy)methyl]ferrocene 在 CuSO₄*5H₂O 、 sodium ascorbate 作用下， 以 水 、 丙酮 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  A Highly Selective Redox, Chromogenic, and Fluorescent Chemosensor for Hg²⁺in Aqueous Solution Based on Ferrocene–Glycine Bioconjugates

  摘要：

  The synthesis, electrochemical, optical, and metal-cation-sensing properties of ferrocene glycine conjugates C30H38O8-N8Fe (2) and C20H24O4N4Fe (3) have been documented. Both compounds 2 and 3 behave as very selective redox (Delta E-1/2 = 217 mV for 2 and Delta E-1/2 = 160 mV for 3), chromogenic, and fluorescent chemosensors for Hg2+ cations in an aqueous environment. The considerable changes in their absorption spectra are accompanied by the appearance of a new low-energy peak at 630 nm (2, epsilon = 1600M(-1) cm(-1) ; 3, epsilon = 822M(-1) cm(-1)). This is also accompanied by a strong color change from yellow to purple, which allows a prospective for the "naked eye" detection of Hg2+ cations. These chemosensors present immense brightness and fluorescence enhancement (chelation-enhanced fluorescence = 91 for 2 and 42 for 3) following Hg2+ coordination within the limit of detection for Hg2+ at 7.5 parts per billion.

  DOI：

  10.1021/ic200573m
• 作为产物：
  描述：

  1,1'-dihydroxymethylferrocene 、 3-溴丙炔 在 NaOH 作用下， 以 二甲基亚砜 为溶剂， 以56%的产率得到1,1'-bis[(2-propyn-1-yloxy)methyl]ferrocene
  参考文献：
  名称：

  –C – H···O超分子合成子合成单和双炔基取代的二茂铁及其晶体工程

  摘要：

  单和双炔基取代的二茂铁络合物，[的Fc（CH 2 OCH 2 C ^ CH）Ñ ]，2 - 3（2：Ñ  = 1; 3：Ñ  = 2; FC =二茂铁）已经从在室温下的反应合成单和1,1'-二羟甲基二茂铁，Fc（CH 2 OH）n，1a - b（1a：n  = 1; 1b：n  = 2）和炔丙基溴，收率不高。这些新的二茂铁衍生物的特征在于质量，IR，1通过单晶X射线衍射研究明确地确定了H，13 C NMR光谱以及化合物2和3的分子结构。晶体结构分析表明，2和3由无限的1D之字形氢键链和2D微孔氢键分子网络组成，通过分子间C-H···O氢键连接。2和3的分子结构都通过C–H···π相互作用进一步稳定。

  DOI：

  10.1016/j.jorganchem.2009.11.017

文献信息

• Click-generated triazole based ferrocene-carbohydrate bioconjugates: A highly selective multisignalling probe for Cu(II) ions
  作者：Arunabha Thakur、Sinjinee Sardar、Sundargopal Ghosh

  DOI：10.1007/s12039-012-0321-6

  日期：2012.11

  Two Cu2+-specific colorimetric sensors, based on ferrocene-carbohydrate bioconjugates, 2, C46H56O20N6Fe and 3, C28H33O10N3Fe were designed and synthesized in good yields. Both the compounds, 2 and 3, behave as very selective and sensitive chromogenic and electrochemical chemosensor for Cu2+ ion in aqueous environment (CH3CN/H2O (2:8, v/v). The analytical detection limit (ADL) for receptor 2 was 7.5 × 10−7 M. The considerable changes in their absorption spectra of 2 and 3 are accompanied by the appearance of a new low energy (LE) peak at 630 nm (2: ε = 1600 M−1 cm−1 and 3: 822 M−1 cm−1). This is further accompanied by a strong colour change from yellow to dark green that allows the prospective for ‘naked eye’ detection of Cu2+ ion.

  本研究设计并合成了两种基于二茂铁-碳水化合物生物共轭物的 Cu2+ 特异性比色传感器 2（C46H56O20N6Fe）和 3（C28H33O10N3Fe），产量良好。2 和 3 这两种化合物在水环境（CH3CN/H2O (2:8, v/v)）中对 Cu2+ 离子具有非常高的选择性和灵敏度。受体 2 的分析检出限（ADL）为 7.5 × 10-7 M。受体 2 和受体 3 的吸收光谱发生了很大变化，在 630 nm 处出现了一个新的低能量（LE）峰（受体 2：ε = 1600 M-1 cm-1 和受体 3：822 M-1 cm-1）。此外，还伴随着从黄色到深绿色的强烈颜色变化，这使得 "肉眼 "检测 Cu2+ 离子成为可能。
• A triazole tethered triferrocene derivative as a selective chemosensor for mercury(II) in aqueous environment
  作者：Dipendu Mandal、Arunabha Thakur、Sundargopal Ghosh

  DOI：10.1016/j.poly.2012.06.060

  日期：2013.3

  Abstract The synthesis, electrochemical, optical and cation-sensing properties of two triazole tethered ferrocene derivatives, C25H25ON3Fe2, 2 and C40H40O2N6Fe3, 3 are presented. The solid state structure of compound 2 has been established by X-ray diffraction analysis which reveals that the unit cell of molecule 2 consists of 3-D helical chain formed via CH⋯N interaction and π⋯π stacking. The complexation

  摘要介绍了两种三唑系链的二茂铁衍生物C25H25ON3Fe2，2和C40H40O2N6Fe3，3的合成，电化学，光学和阳离子传感性能。通过X射线衍射分析已建立了化合物2的固态结构，该结构揭示了分子2的晶胞由通过CH⋯N相互作用和π⋯π堆积形成的3-D螺旋链组成。可以从氧化还原位移或Hg2 +和Cu2 +阳离子的视觉输出响应（比色法）推断受体的络合特性。这些配体的共同结构特征是存在其他二茂铁部分作为氧化还原单元。有趣的是，在水（CH3CN / H2O，2/8）存在的情况下，对Hg2 +的氧化还原和比色响应得以保留，可以用于比对其他竞争性阳离子的水性环境中Hg2 +的选择性比色检测。吸收光谱的变化伴随有一个新的低能（LE）峰出现在大约。2的626 nm和3的632 nm（2：e = 669 M-1 cm-1和3：e = 1150 M-1 cm-1），这是由于CH3CN中Hg2 +阳离子的颜色从黄色变为紫色/
• An Efficient Ferrocene Derivative as a Chromogenic, Optical, and Electrochemical Receptor for Selective Recognition of Mercury(II) in an Aqueous Environment
  作者：Arunabha Thakur、Sundargopal Ghosh

  DOI：10.1021/om201073g

  日期：2012.2.13

  The synthesis, electrochemical, optical, and cation-sensing properties of two triazole-tethered ferrocenyl benzylacetate derivatives, C36H36O6N6Fe (2) and C23H23O3N3Fe (3), are presented. The binding event of both the receptors can be inferred either from a redox shift (2, Delta E-1/2 = 106 mV for Hg2+ and Delta E-1/2 = 187 mV for Ni2+; 3, Delta E-1/2 = 167 mV for Hg2+ and Delta E-1/2 = 136 mV for Ni2+) or a highly visual output response (colorimetric) for Hg2+, Ni2+, and Cu2+ cations. Remarkably, the redox and calorimetric responses toward Hg2+ are preserved in the presence of water (CH3CN/H2O, 2/8), which can be used for the selective calorimetric detection of Hg2+ in an aqueous environment over Ni2+ and Cu2+ cations. The changes in the absorption spectra are accompanied by the appearance of a new low-energy (LE) peak at 625 nm for both compounds 2 and 3 (2, epsilon = 2500 M-1 cm(-1); 3, epsilon = 1370 M-1 cm(-1)), due to a change in color from yellow to purple for Hg2+ cations in CH3CN/H2O (2/8).
• Ferrocene-containing macrocyclic triazoles for the electrochemical sensing of dihydrogen phosphate anion
  作者：Chun-Tao Li、Qian-Yong Cao、Jia-Jin Li、Zhong-Wei Wang、Bo-Na Dai

  DOI：10.1016/j.ica.2016.04.047

  日期：2016.8

  Two novel ferrocene-containing macrocyclic triazoles (L1 and L2) and their acyclic analogs (L3 and L4) were easily prepared by "click" reaction. The anions binding abilities of L1-L4 were evaluated by cyclic voltammetry and differential pulse voltammetry methods. The results revealed that the receptors L1-L4 have exclusive electrochemical sensing of H2PO4, with the shift in redox potentials of L1-L4 towards the cathodic values. The binding mechanisms between the receptors and H2PO4 were examined by H-1 NMR titrations and density functional theory (DFT) calculations. (C) 2016 Elsevier B. V. All rights reserved.