ferrocenyl barbituric acid | 51804-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ferrocenyl barbituric acid
• 英文别名: 5-ferrocenylmethylenebarbituric acid；cyclopenta-1,3-diene;5-(cyclopenta-2,4-dien-1-ylmethylidene)-1,3-diazinane-2,4,6-trione;iron(2+)
• CAS: 51804-23-0
• 化学式: C₁₅H₁₂FeN₂O₃
• 分子量: 324.119
• InChiKey: QQSGCVISCRRXHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 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：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  ferrocenyl barbituric acid 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到5-ferrocenylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Second harmonic generation in ferrocene based hydrogen bonded assemblies

  摘要：

  Supramolecular assemblies formed by electron donors and acceptors might possess very large optical nonlinearity, even larger than the sum of the constituents if they form noncentrosymmetric networks. To probe this hypothesis we have functionalized barbituric acid, by condensing it with ferrocene carboxaldehyde to give 1, a hydrogen bond donor-acceptor-donor (H-DAD). This molecule complements the hydrogen bond donor acceptor sites of 2,6-diaminopyridine (2) which is a hydrogen bond acceptor-donor-acceptor (H-ADA). 2,6-Diaminopyridine was further functionalized with acetyl ferrocene to give 3, which forms complexes with 1. Complex formation was studied using nuclear magnetic resonance spectroscopy. The second order nonlinear optical (NLO) response of these hydrogen bonded assemblies has been probed by hyper Rayleigh scattering (HRS) measurements and was found to be maximum when I was mixed with five equivalents of 3. A plausible explanation for the formation of 1:5 complex was given on the basis of control experiments with 4, a methylated analog of 1, and the addition of a strong hydrogen bond acceptor solvent, methanol. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00960-3
• 作为产物：
  描述：

  巴比妥酸 、 二茂铁甲醛 以 乙醇 为溶剂， 以77%的产率得到ferrocenyl barbituric acid
  参考文献：
  名称：

  带有汉密尔顿型受体的共价改性 MoS2，用于通过多个氢键识别氧化还原活性二茂铁-巴比妥酸盐客体

  摘要：

  汉密尔顿型识别基序在 1T-MoS 2表面实现，其中通过氢键发生主客体相互作用，用于巴比妥酸盐的电化学传感。

  DOI：

  10.1002/chem.202301474

文献信息

• Ferrocene derivatives
  申请人：UNITED STATES OF AMERICA NAVY

  公开号：US03755311A1

  公开（公告）日：1973-08-28

  Compounds useful as burning rate catalysts for solid propellants characterized by low volatility and having the formula ARE DISCLOSED WHEREIN R is O, NR' and S and each R' is hydrogen, lower alkyl, phenyl, cyano and nitro.

  公开了作为固体推进剂燃烧速率催化剂有用的化合物，其特征是挥发性低，并且具有以下公式：其中R为O、NR'和S，每个R'为氢、低烷基、苯基、氰基和硝基。
• Green Chemistry Approaches to Condensation Reactions of Formylferrocene with Active Methylene Containing Compounds
  作者：Yinjuan Bai、Jun Lu、Haiying Gan、Zhenjun Wang、Zhen Shi

  DOI：10.1081/sim-200026298

  日期：2004.9

  The condensation reactions of formylferrocene with active methylene-containing compounds were achieved by microwave irradiation, grinding or heating in water, in moderate to good yields. The structures were confirmed by H-1 NMR, C-13 NMR, IR spectra, and elemental analyses.
• Some Acyl Ferrocenes and their Reactions
  作者：P. J. Graham、R. V. Lindsey、G. W. Parshall、M. L. Peterson、G. M. Whitman

  DOI：10.1021/ja01570a027

  日期：1957.7
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.7.3.4, page 293 - 295
  作者：

  DOI：——

  日期：——
• Enhancement of Quadratic Nonlinearity via Multiple Hydrogen-Bonded Supramolecular Complex Formation
  作者：Mily Bhattacharya、Ashoka G. Samuelson、Puspendu K. Das

  DOI：10.1021/jp0721651

  日期：2007.6.1

  The formation and quadratic nonlinearity of a multiple hydrogen-bonded 1:1 supramolecular complex 1.2 between the 2,6-diaminopyridine-based Lambda-shaped molecule, 1, and ferrocenyl barbituric acid, 2, in solution have been investigated by the hyper-Rayleigh scattering (HRS) and NMR techniques. A 6-fold increase in the molecular hyperpolarizability (beta) of the complex 1.2 over the sum of the molecular hyperpolarizabilities of the components 1 and 2 is seen. Such a significant enhancement in beta is attributed to the alignment of the molecular dipoles of 1 and 2 in the 2D plane leading to the creation of a large dipole moment in the plane of the supramolecular complex. Depolarized HRS experiments led to the determination of the in-plane polarization components of beta of the supramolecular complex 1.2. The component of beta in the direction of the dipole moment is large. This investigation exemplifies the role of multiple hydrogen bonds in stabilizing a 2D supramolecular architecture leading to a large enhancement of molecular nonlinearity.