4-chlorophenyl ferrocenecarboxylate | 496917-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-chlorophenyl ferrocenecarboxylate
• 英文别名: (4-chlorophenyl)-1-ferrocenoate；(4-chlorophenyl) cyclopenta-1,3-diene-1-carboxylate;cyclopenta-1,3-diene;iron(2+)
• CAS: 496917-04-5
• 化学式: C₁₇H₁₃ClFeO₂
• 分子量: 340.589
• InChiKey: QVZOKSQZXVWTGS-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

• 作为产物：
  描述：

  ferrocenoyl chloride 、 对氯苯酚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 4-chlorophenyl 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

• 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.