4-bromophenyl ferrocenecarboxylate | 496917-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-bromophenyl ferrocenecarboxylate
• 英文别名: (4-bromophenyl) cyclopenta-1,3-diene-1-carboxylate;cyclopenta-1,3-diene;iron(2+)
• CAS: 496917-09-0
• 化学式: C₁₇H₁₃BrFeO₂
• 分子量: 385.04
• InChiKey: VUQRRKHBQDRAOL-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：

  4-溴苯酚 、 fluorocarbonylferrocene 在 4-二甲氨基吡啶 作用下， 以 further solvent(s) 为溶剂， 以60%的产率得到4-bromophenyl ferrocenecarboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2005.08.015

文献信息

• Functionalized ferrocenes: The role of the para substituent on the phenoxy pendant group
  作者：José L. Vera、Jorge Rullán、Natasha Santos、Jesús Jiménez、Joshua Rivera、Alberto Santana、Jon Briggs、Arnold L. Rheingold、Jaime Matta、Enrique Meléndez

  DOI：10.1016/j.jorganchem.2013.10.002

  日期：2014.1

  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.