3-ferrocenyl-1-(4'-hydroxyphenyl)-prop-2-en-1-one | 474640-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ferrocenyl-1-(4'-hydroxyphenyl)-prop-2-en-1-one
• 英文别名: 3-ferrocenyl-1-(p-hydroxyphenyl)-prop-2-en-1-one；1-ferrocenyl-3-(p-hydroxyphenyl)-prop-2-ene-1-one；cyclopenta-1,3-diene;3-cyclopenta-2,4-dien-1-yl-1-(4-hydroxyphenyl)prop-2-en-1-one;iron(2+)
• CAS: 474640-91-0
• 化学式: C₁₉H₁₆FeO₂
• 分子量: 332.182
• InChiKey: WNDSHFLIYLCZLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  22
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ferrocenyl-1-(4'-hydroxyphenyl)-prop-2-en-1-one 、 4-tetradecyloxybenzoyl chloride 以 吡啶 为溶剂， 反应 8.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis, Electrochemical, and Thermal Properties of [3]Ferrocenophane-Containing Chalcone Derivatives

  摘要：

  [合成并表征了具有苯环（3a-3d）或萘环（3e-3f）的含二茂铁查尔酮衍生物。与含二茂铁的查耳酮相比，含二茂铁的查耳酮的[3]电位阴极移动了 ~70-80 mV，这表明前者更容易因失去一个电子而被氧化。差示扫描量热法和偏振光学显微镜研究了所制备化合物的热行为。末端烷基链为 14 个碳原子的化合物 3f 显示出介相，而其他化合物则没有介相，在加热和冷却循环中显示出晶体多态相变或简单的熔化和冻结过程。

  DOI：

  10.1071/ch14529

文献信息

• A disulfide-linked conjugate of ferrocenyl chalcone and silicon(<scp>iv</scp>) phthalocyanine as an activatable photosensitiser
  作者：Janet T. F. Lau、Xiong-Jie Jiang、Dennis K. P. Ng、Pui-Chi Lo

  DOI：10.1039/c2cc37251g

  日期：——

  A novel bis(ferrocenyl chalcone) silicon(IV) phthalocyanine has been prepared in which the disulfide linker can be cleaved by dithiothreitol. The separation of the ferrocenyl quencher and the phthalocyanine core greatly enhances the fluorescence emission, singlet oxygen production and in vitro photocytotoxicity.

  一种新型的双(二茂铁基查尔酮)硅(IV)酞菁已制备完成，其中二硫键连接体可通过二硫苏糖醇裂解。二茂铁淬灭剂与酞菁核心的分离极大地增强了荧光发射、单线态氧的产生以及体外光细胞毒性。
• Ferrocenyl pyrazolines: Preparation, structure, redox properties and DFT study on regioselective ring-closure
  作者：Virág Zsoldos-Mády、Oliver Ozohanics、Antal Csámpai、Veronika Kudar、Dávid Frigyes、Pál Sohár

  DOI：10.1016/j.jorganchem.2009.09.007

  日期：2009.12

  were investigated. With methylhydrazine, formation of two regioisomeric pairs of pyrazolines and pyrazoles was observed. The ratio of the products varied with the solvent and temperature. Transformation of 5-ferrocenyl-N-substituted pyrazolines into pyrazoles was systematically studied and DDQ was found to be the most suitable reagent. Mechanism of the cyclization reactions taking place under kinetic-

  1-苯基-3-二茂铁基-2-丙烯-1-酮的环缩合（1）与RNHNH2肼的关系以及取代基依赖性产物的分布进行了研究。用甲基肼观察到形成了两个对位的吡唑啉和吡唑区域异构体。产物的比例随溶剂和温度而变化。系统研究了5-二茂铁基-N-取代的吡唑啉向吡唑的转化，发现DDQ是最合适的试剂。DFT计算支持在动力学和热力学控制下发生环化反应的机理。EI MS还研究了吡唑啉向吡唑的转化的能量依赖性。新化合物的结构测定是通过IR，MS和NMR方法进行的，包括2D-HMQC，2D-HMBC，DEPT和DIFFNOE测量。对于两种化合物，还通过X射线衍射证明了结构。
• Ferrocenyl-contained dendritic-like antioxidants with dihydropyrazole and pyrazole as the core: investigations into the role of ferrocenyl group and structure–activity relationship on scavenging radical and protecting DNA
  作者：Pei-Ze Li、Zai-Qun Liu

  DOI：10.1016/j.tet.2013.08.053

  日期：2013.11

  Eight ferrocenyl and three corresponding phenyl dendritic-like antioxidants with dihydropyrazole or pyrazole as the core were synthesized and their antioxidant abilities to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+center dot)) and to protect DNA against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation were evaluated. It was found that the antioxidant abilities of almost all of the ferrocenyl dendritic-like antioxidants are greater than those of the corresponding phenyl dendritic-like antioxidants remarkably. Moreover, the structure-activity relationships of all these dendritic-like antioxidants were investigated in detail. The quantitative contributions of ferrocenyl group, hydroxyl group, and dihydro-structure in the heterocyclic core to the values of n, n(app) and n+n(app) in scavenging ABTS(+center dot) and the values of n in protecting DNA against AAPH-induced oxidation were also calculated. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.