1,1-bis(p-aminophenyl)-2-oxo[4]ferrocenophane | 1384213-51-7

• 英文名称: 1,1-bis(p-aminophenyl)-2-oxo[4]ferrocenophane
• CAS: 1384213-51-7
• 化学式: C₂₆H₂₄FeN₂O
• 分子量: 436.336
• InChiKey: CKLRVTWSIZBSHG-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：

  1-bis(p-acetamidophenyl)-1-phenyl-2-oxo[4]ferrocenophane 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以32%的产率得到1,1-bis(p-aminophenyl)-2-oxo[4]ferrocenophane
  参考文献：
  名称：

  Synthesis and Antiproliferative Effects of [3]Ferrocenophane Transposition Products and Pinacols Obtained from McMurry Cross-Coupling Reactions

  摘要：

  We here report the synthesis and antiproliferative activities of two new series of ferrocenophanes obtained from McMurry cross-coupling reactions of [3]ferrocenophan-1-one with benzophenone, 4-hydroxybenzophenone, 4,4'-dihydroxybenzophenone, and 4,4'-diacetylaminobenzophenone. In addition to the main formation of olefins at reflux, tetrahedral transposition products, resulting from a pinacolic rearrangement, were also isolated in about 10% yields. Lowering the temperature of the reaction to 0 degrees C allowed the isolation of pinacols, which could be transformed into transposition compounds in good yields. Three ferrocenophane compounds have been characterized by X-ray crystallography: 1-(p-hydroxyphenyl)-1-phenyl-2-oxo[4]ferrocenophane (7b), 1,1-dipheny1-2-oxo[4]ferrocenophane (7c), and 1-hydroxy-1[1-hydroxy-1-[3]ferrocenophanyl][3]ferrocenophane (12) crystallize in monoclinic P2(1)/n, triclinic P (1) over bar and monoclinic P2(1)/c space groups, respectively. The antiproliferative effects on hormone-independent breast cancer cells (MDA-MB-231) of the transposition compounds are generally lower than those of their corresponding butene analogues (IC50 values in micromolar versus nanomolar range). In contrast and quite surprisingly, the pinacol complexes are significantly cytotoxic (IC50 in the nanomolar range), among the most cytotoxic ferrocene compounds prepared so far. This antiproliferative activity may be linked to their oxidative cleavage.

  DOI：

  10.1021/om300382h