5-ferrocenyl-1,3-diphenyl-1H-pyrazole | 1201805-69-7

• 英文名称: 5-ferrocenyl-1,3-diphenyl-1H-pyrazole
• 英文别名: 1,3-diphenyl-5-ferrocenyl-pyrazole
• CAS: 1201805-69-7
• 化学式: C₂₅H₂₀FeN₂
• 分子量: 404.294
• InChiKey: ADXRBIQLSGIRKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  5-ferrocenyl-1,3-diphenyl-4,5-dihydro-1H-pyrazole 在 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到5-ferrocenyl-1,3-diphenyl-1H-pyrazole
  参考文献：
  名称：

  二茂铁基吡唑啉：区域选择性闭环的制备，结构，氧化还原性质和DFT研究

  摘要：

  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。

  DOI：

  10.1016/j.jorganchem.2009.09.007

文献信息

• A two-step synthesis of ferrocenyl pyrazole and pyrimidine derivatives based on carbonylative Sonogashira coupling of iodoferrocene
  作者：Csaba Fehér、Árpád Kuik、László Márk、László Kollár、Rita Skoda-Földes

  DOI：10.1016/j.jorganchem.2009.08.029

  日期：2009.12

  A new method for the synthesis of 3-substituted-1-ferrocenyl-2-propyn-1-ones was developed involving carbonylative Sonogashira coupling of iodoferrocene with terminal acetylenes. New ferrocenyl 1,3,5-trisubstituted pyrazoles and 2,4,6-trisubstituted pyrimidines were obtained by the addition-cyclocondensation reaction of the alkynones with hydrazines and guanidinium salts, respectively. The products

  开发了一种新的合成3-取代的1-二茂铁基-2-丙炔-1-酮的方法，该方法涉及碘代二茂铁与末端乙炔的羰基化Sonogashira偶联。通过炔烃分别与肼和胍盐的加成-环缩合反应得到新的二茂铁基1，3，5-三取代的吡唑和2，4，6-三取代的嘧啶。获得的产物具有中等至极好的收率，并通过各种光谱方法进行了表征（1 H NMR，13 C NMR IR，MS）。
• 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.