phenyl ferrocenecarboxylate | 1295-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl ferrocenecarboxylate
• 英文别名: phenyl-1-ferrocenoate；cyclopenta-1,3-diene;iron(2+);phenyl cyclopenta-2,4-diene-1-carboxylate
• CAS: 1295-38-1
• 化学式: C₁₇H₁₄FeO₂
• 分子量: 306.144
• InChiKey: OPDIYHSATVDIJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ferrocenoyl chloride 、 苯酚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl ferrocenecarboxylate
  参考文献：
  名称：

  Functionalized ferrocenes: The role of the para substituent on the phenoxy pendant group

  摘要：

  Six ferrocenecarboxylates with phenyl, 4-(1H-pyrrol-1-yl)phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl as pendant groups were synthesized and fully characterized by spectroscopic, electrochemical and X-ray diffraction methods. The anti-proliferative activity of these complexes were investigated in hormone dependent MCF-7 breast cancer and MCF-10A normal breast cell lines, to determine the role of the para substituent on the phenoxy pendant group. The 4-fluorophenyl ferrocenecarboxylate is inactive in both cell lines while 4-(1H-pyrrol-1-yl) phenyl ferrocenecarboxylate is highly cytotoxic in both cell lines. 4-chlorophenyl and 4-bromophenyl ferrocenecarboxylates have moderate to good anti-proliferative activity in MCF-7 and low anti-proliferative activity on normal breast cell line, MCF-10A whereas the 4-iodophenyl analog is highly toxic on normal breast cell line. The phenyl ferrocenecarboxylate has proliferative effects on MCF-7 and is inactive in MCF-10A. Docking studies between the complexes and the alpha-estrogen receptor (ER alpha) were performed to search for key interactions which may explain the anti-proliferative activity of 4-bromophenyl ferrocenecarboxylate. Docking studies suggest the anti-proliferative activity of these ferrocenecarboxylates is attributed to the cytotoxic effects of the ferrocene group and not to anti-estrogenic effects. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.10.002

文献信息

• Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
  作者：Changyu Huang、Jinpeng Li、Jiaquan Wang、Qingshu Zheng、Zhenhua Li、Tao Tu

  DOI：10.1007/s11426-020-9883-3

  日期：2021.1

  interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments

  酰胺CN的裂解在合成化学，生物过程和制药工业中引起了广泛的兴趣。过渡金属，豪华配体或过量的碱对转化始终至关重要。在这里，我们开发了仅催化量碱的无过渡金属的氢键助酰胺化酰胺。控制实验，密度泛函理论（DFT）计算和动力学研究支持了氢键在协助酯化中所起的关键作用。除了广泛的底物范围和出色的官能团耐受性外，该碱催化方案还补充了传统的过渡金属催化的酰胺酯化反应，并为有机合成和制药行业催化裂解酰胺CN键提供了新途径。
• N-Heterocyclic carbene catalysed aerobic oxidation of aromatic aldehydes to aryl esters using boronic acids
  作者：Panjab Arde、B. T. Ramanjaneyulu、Virsinha Reddy、Apurv Saxena、R. Vijaya Anand

  DOI：10.1039/c1ob06566a

  日期：——

  The organocatalytic behavior of N-heterocyclic carbenes in the aerobic oxidation of aromatic aldehydes to esters with boronic acids has been explored. This transition metal-free protocol allows access to a wide variety of aromatic esters in good to excellent yields under mild reaction conditions.

  研究了N-杂环卡宾在芳香醛与硼酸的好氧氧化为酯反应中的有机催化行为。这种无过渡金属的方法可以在温和的反应条件下以良好的产率获得各种芳族酯。
• An investigation of the chemistry of ferrocenoyl derivatives. The synthesis and reactions of ferrocenoyl imidazolide and its derivatives
  作者：Christopher Imrie、Leanne Cook、Demetrius C Levendis

  DOI：10.1016/s0022-328x(01)00915-9

  日期：2001.12

  red crystalline compound that is stable at <5 °C in the dark and it acts as an efficient ferrocenoyl equivalent. It reacts rapidly with alkoxides to give esters and with thiolates to give thioesters. Its reaction with Lawesson's reagent gave diferrocenoyl disulfide. Attempts to make diferrocenoyl peroxide by reacting ferrocenoyl imidazolide with hydrogen peroxide were unsuccessful. Ferrocenoyl imidazolide

  二茂铁酰基咪唑啉化物易于从二茂铁羧酸一步合成。它是一种红色结晶化合物，在黑暗中于<5°C时稳定，可作为有效的二茂铁酰基等同物。它与醇盐快速反应生成酯，与硫醇盐迅速生成硫酯。它与Lawesson试剂的反应产生了二亚铁二茂铁酰基二硫化物。通过使二茂铁酰基咪唑啉化物与过氧化氢反应来制备二茂铁酰基过氧化氢的尝试是失败的。二茂铁酰基咪唑啉化物通过与二茂铁基-锂反应，一步转化为三茂铁基甲醇和二茂铁基酮。描述了二茂铁基苯基硫化物和二茂铁基二硫化物的X射线晶体结构。
• N-ferrocenoyl benzotriazole: A convenient tool for the synthesis of ferrocenoyl esters
  作者：Deniz Hür、Sultan Funda Ekti、Hakan Dal

  DOI：10.1016/j.jorganchem.2009.11.015

  日期：2010.4

  A new synthesis methodology has been presented for the preparation of the ferrocenoyl esters. Ferrocene carboxylic acid was derivatized using direct 1H-benzotriazole/SOCl2 methodology to prepare N-ferrocenoyl benzotriazole as a convenient tool for the functionalization of ferrocene ring. N-ferrocenoyl benzotriazole was reacted with alcohols in mild conditions to prepare ferrocenoyl esters in high purity and in good yield. The solid state structure of benzyl-1-ferrocenoate, 2f, has also been determined by X-ray crystallography. In the crystal structure, intermolecular C-H center dot center dot center dot O hydrogen bonds link the molecules into a two-dimensional network. The pi center dot center dot center dot pi contacts between the cyclopentadiene rings and cyclopentadiene and phenyl rings, [centroid-centroid distances = 3.296(1) and 3.750(1) angstrom] may further stabilize the structure. Two weak C-H center dot center dot center dot pi interactions are also found. (C) 2009 Elsevier B. V. All rights reserved.
• Synthesis of ferrocenoate esters, amides and other ferrocenoyl derivatives using ferrocenoyl fluoride. A comparison of the reactions of ferrocenoyl fluoride in [bmim][BF4] with the microwave-promoted solvent-free reactions of ferrocenoyl fluoride
  作者：Christopher Imrie、Elago R.T. Elago、Nadia Williams、Cedric W. McCleland、Pieter Engelbrecht

  DOI：10.1016/j.jorganchem.2005.08.015

  日期：2005.11

  Simple, efficient and convenient routes for the synthesis of ferrocenoyl derivatives are described. They involve either the reaction of nucleophilic compounds and DMAP with ferrocenoyl fluoride in [bmim][BF4] or the solvent-free reactions of nucleophilic compounds with ferrocenoyl fluoride promoted by microwaves. (c) 2005 Elsevier B.V. All rights reserved.