5-ferrocenylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione | 387392-26-9

• 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: 5-ferrocenylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: [(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]ferrocene；cyclopenta-1,3-diene;5-(cyclopenta-1,3-dien-1-ylmethylidene)-1,3-dimethyl-1,3-diazinane-2,4,6-trione;iron(2+)
• CAS: 387392-26-9
• 化学式: C₁₇H₁₆FeN₂O₃
• 分子量: 352.173
• InChiKey: MNCFJBJFVULQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• Preparation and structure of zinc complexes containing pincer ligands and their application for Knoevenagel condensation in water
  作者：Wei-Guo Jia、Dan-Dan Li、Hui Zhang、Yuan-Chen Dai、En-Hong Sheng

  DOI：10.1080/00958972.2014.978308

  日期：2015.1.17

  have been characterized by elemental analysis, NMR and IR spectra. The molecular structures of 2a and 2b have been determined by X-ray crystallography. Complex 2b is efficient in catalyzing Knoevenagel condensation of ferrocenecarboxaldehyde with activated methylene compounds in water. Graphical Abstract

  两种具有 Pybox 配体的锌配合物，2,6-双[4',4'-二甲基恶唑啉-2'-基]吡啶 (Dm-pybox) (1a) 和 2,6-双[4'-异丙基恶唑啉-2'- yl]吡啶（i-Pr-pybox）（1b），已被合成和表征。氯化锌与基于吡啶的钳形配体的反应分别导致 (Dm-Pybox)ZnCl2 (2a) 和 (i-Pr-Pybox)ZnCl2 (2b) 的形成。两种配合物均已通过元素分析、核磁共振和红外光谱表征。2a 和 2b 的分子结构已通过 X 射线晶体学确定。配合物 2b 可有效催化二茂铁甲醛与活化的亚甲基化合物在水中的 Knoevenagel 缩合反应。图形概要