1,3-diferrocenyl-2-propen-1-one | 105404-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-diferrocenyl-2-propen-1-one
• 英文别名: 1,3-diferrocenyl-2-propenone；1,3-bisferrocenyl-2-propen-1-one；1-ferrocenyl-3-ferrocenyl-3-prop-2-ene-1-one；(2E)-1,3-diferrocenylprop-2-en-1-one；β-ferrocenylvinyl(ferrocenyl)ketone；1,3-diferrocenylprop-2-en-1-one；1,3-ferrocenyl-2-propen-1-one；FcC(O)CHCHFc
• CAS: 105404-21-5
• 化学式: C₂₃H₂₀Fe₂O
• 分子量: 424.105
• InChiKey: HGXNKEVWYPLZLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diferrocenyl-2-propen-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3,5-diferrocenyl-4,5-dihydropyrazole
  参考文献：
  名称：

  Ferrocene-based sulfonyl dihydropyrazole derivatives: Synthesis, structure, electrochemistry and effect on thermal decomposition of NH4ClO4

  摘要：

  Three ferrocene-based sulfonyl-substituted dihydropyrazoles 3a-c have been synthesized, from the corresponding cell-unsaturated diketones, and fully characterized. The crystal structures of 3a-c have been confirmed by X-ray crystallography, and electrochemistry behaviors of 3a-c have been examined by cyclic voltammetry (CV). Representatively, the mechanism of the electron transfer in redox process of 3a has been verified by density functional theory (DFT) calculation. It has been found that the activity of catalytic decomposition of ammonium perchlorate (AP) is significantly lowered (by 62.9-104.7 degrees C) with an addition of 3a-c. We expect that the ferrocene-based sulfonyl dihydropyrazole derivatives would have a great value in burning rate catalyst as composite solid propellants. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.03.013
• 作为产物：
  描述：

  二茂铁甲醛 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 氯仿 为溶剂， 以54%的产率得到1,3-diferrocenyl-2-propen-1-one
  参考文献：
  名称：

  Reaction of formylferrocene and formylcymantrene with chloroform under interphase catalysis conditions and synthesis of ?-metallocenylglycolic acids

  摘要：

  DOI：

  10.1007/bf01418009

文献信息

• The catalysis, synthesis and characterization of ferrocenylchalcone
  作者：Yu-Ting Liu、Li Feng、Da-Wei Yin

  DOI：10.1007/s11164-012-0810-8

  日期：2013.9

  and reaction times on the yield of ferrocenylchalcone derivatives are discussed. The optimal conditions of synthesis reaction have been selected: the catalyst was KF/Al2O3, n(acetyl ferrocene)/n(formal dehyde) = 1:1.2. The structures of the products were characterized by melting point test, IR, 1HNMR, 13CNMR and elemental analysis.

  实验中，以固体为催化剂，通过乙酰基二茂铁与芳香醛的反应合成了八种二茂铁基查耳酮衍生物。讨论了催化剂的影响，原料的摩尔比和反应时间对二茂铁基查耳酮衍生物产率的影响。选择了最佳的合成反应条件：催化剂为KF / Al 2 O 3，n（乙酰基二茂铁）/ n（甲醛）＝ 1：1.2。通过熔点测试，IR，1 HNMR，13 CNMR和元素分析表征产物的结构。
• Design and synthesis of ferrocene‐tethered pyrazolines and pyrazoles: Photophysical studies, protein‐binding behavior with bovine serum albumin, and antiproliferative activity against MDA‐MB‐231 triple negative breast cancer cells
  作者：Koena Ghosh、Nipa Nayek、Subhomoy Das、Nabendu Biswas、Samraj Sinha

  DOI：10.1002/aoc.6248

  日期：2021.7

  We report synthesis and characterization of a series of ferrocene-pyrazoline and pyrazole hybrids and demonstrate their biomedical applications. All new compounds were identified with the help of spectroscopic techniques and single-crystal X-ray analysis. The compounds from both the series show fluorescent activity. The effect of C5 aryl substituent on the luminescent behavior of the parent system

  我们报告了一系列二茂铁-吡唑啉和吡唑杂化物的合成和表征，并展示了它们的生物医学应用。在光谱技术和单晶 X 射线分析的帮助下，鉴定了所有新化合物。这两个系列的化合物都显示出荧光活性。C5芳基取代基对母体系统发光行为的影响通过研究它们的吸收和发射行为来跟踪。通过使用激发波长 290 nm 的荧光猝灭实验检测了选定的具有 C5 2-萘基取代基 ( 4g ) 的二茂铁基吡唑啉与牛血清白蛋白 (BSA)的结合亲和力。配体4g淬灭了 BSA 的固有荧光。4g之间强绑定观察到 BSA 具有 105 M-1 量级的复合物形成的平衡常数。一系列二茂铁-吡唑啉和吡唑（4f , 4g , 4h , 5f , 5g , 和5h）的体外抗癌活性被测试对不依赖激素的三阴性乳腺癌细胞MDA-MB-231 ，其中注意到最大抑制效力。为4小时以IC 50 3.61毫克毫升值-1。
• Synthesis of Ferrocenyl-Substituted 3-Cyano-2-methylpyridines
  作者：Katsuyoshi Shibata、Isamu Katsuyama、Masaki Matsui、Hiroshige Muramatsu

  DOI：10.1246/bcsj.63.3710

  日期：1990.12

  Ferrocenyl-substituted 3-cyano-2-methylpyridines were easily prepared by the sonication of α,β-unsaturated carbonyl compounds substituted by ferrocenes in acetonitrile in the presence of potassium t-butoxide.

  通过在叔丁醇钾存在下，将取代有二茂铁的α,β-不饱和羰基化合物在乙腈中进行声波处理，可以轻松地制备出2-甲基-3-氰基吡啶的二茂铁基取代物。
• Synthesis, crystal structure and redox properties of dihydropyrazole-bridged ferrocene-based derivatives
  作者：Heng-Dong Li、Zai-He Ma、Kun Yang、Li-Li Xie、Yao-Feng Yuan

  DOI：10.1016/j.molstruc.2012.05.026

  日期：2012.9

  hydrate, then acylation with 3-(ethoxycarbonyl)propionyl chloride directly in high yields and purity. All of these compounds were characterized by MS, IR, 1 H NMR, 13 C NMR and elemental analysis. The relationship between the structure and redox properties was investigated based on the results of single crystal X-ray structure determinations and cyclic voltammetry. The mechanism of the electron transfer

  摘要 采用相应的查耳酮与水合肼直接酰化3-（乙氧基羰基）丙酰氯，以高收率和高纯度制备了二氢吡唑桥连二茂铁基衍生物。所有这些化合物均通过 MS、IR、 1 H NMR、 13 C NMR 和元素分析进行​​表征。基于单晶X射线结构测定和循环伏安法的结果研究了结构与氧化还原性能之间的关系。通过密度泛函理论 (DFT) 计算验证了代表性化合物 4b 的电子转移机制。
• Functional ionic liquid [bmim][Sac] mediated synthesis of ferrocenyl thiopropanones via the “dual activation of the substrate by the ionic liquid”
  作者：Atul Kumar、Suman Srivastava、Garima Gupta、Promod Kumar、Jayanta Sarkar

  DOI：10.1039/c3ra22543g

  日期：——

  An artificial sweetener saccharin based functional ionic liquid [bmim][Sac] mediated synthesis has been explored for the first time in the organometallic field. The ionic liquid plays a critical role as the catalyst for substrate activation by directly facilitating the “solvent-free” Michael addition of thiol to ferrocenyl enone. The key to the present methodology is the dual hydrogen bonding of the saccharinate anion that is believed to play a crucial role in thiol activation. All the synthesized ferrocene thiopropanones were examined for their in vitro anti-proliferative activity.

  首次在有机金属领域探讨了一种以人工甜味剂糖精为基础的功能性离子液体[bmim][Sac]介导的合成。这种离子液体在底物活化中作为催化剂发挥了关键作用，直接促进了“无溶剂”条件下硫醇与铁烯酮的迈克尔加成。目前方法的关键是糖精阴离子的双氢键作用，据信在硫醇活化中起到了重要作用。所有合成的铁烯硫丙酮均进行了体外抗增殖活性检测。