ethyl 1,2,3,4-tetrahydro-4-ferrocenyl-6-methyl-2-oxopyrimidine-5-carboxylate | 571177-22-5

• 英文名称: ethyl 1,2,3,4-tetrahydro-4-ferrocenyl-6-methyl-2-oxopyrimidine-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-4-ferrocenyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• CAS: 571177-22-5
• 化学式: C₁₈H₂₀FeN₂O₃
• 分子量: 368.215
• InChiKey: URKDHTNOWIXAGC-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

• 作为反应物：
  描述：

  甲醇 、 ethyl 1,2,3,4-tetrahydro-4-ferrocenyl-6-methyl-2-oxopyrimidine-5-carboxylate 在 四丁基氢氧化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到ethyl 1,2,3,4-tetrahydro-4-ferrocenyl-(1-methoxymethyl)-6-methyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones

  摘要：

  A series of ferrocene-containing mono- and bis-dihydropyrimidines (DHP's) were prepared by boric acid mediated three-component Biginelli reactions of formyl- and 1,1'-diformylferrocene, 1,3-dioxo-components and urea. A few further transformations including hydrogenolysis of a benzyl 4-ferrocenyl-DHP-5-carboxylate were also performed. Novel cis-fused saturated pyrimido[4,5-d]pyrimidine-2,7(1H, 3H)-diones incorporating [3]-ferrocenophane moiety were constructed by means of iron(III)-catalyzed Biginelli-like condensations of 1,1'-diformylferrocene with urea and in situ generated methyl ketone-derived silyl enol ethers. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.06.017
• 作为产物：
  描述：

  、 乙酰乙酸乙酯 在 silicomolybdic heteropolyacid 、 溶剂黄146 作用下， 反应 2.0h， 生成 ethyl 1,2,3,4-tetrahydro-4-ferrocenyl-6-methyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid

  摘要：

  通过甲酰基二茂铁、1,3-二羰基成分和脲/硫脲的一锅 Biginelli 反应，制备了一系列含二茂铁的二氢嘧啶（DHPs）。该反应由商用 Keggin 杂多酸（H4SiMo12O40）催化，它是一种安全、清洁且可回收的催化剂。为了提高反应的产率并阐明其机理，我们研究了三种不同的合成方案。此外，还分离出了竞争性 Knoevenagel 反应的中间产物。该方法操作简单，能以非常高的产率获得含有二茂铁的高取代二氢嘧啶。催化剂可以使用和回收，而不会明显丧失催化活性。

  DOI：

  10.1007/s11164-015-2067-5

文献信息

• Impact of the ferrocenyl group on cytotoxicity and KSP inhibitory activity of ferrocenyl monastrol conjugates
  作者：Anna Wieczorek-Błauż、Karolina Kowalczyk、Andrzej Błauż、Anna Makal、Sylwia Pawlędzio、Chatchakorn Eurtivong、Homayon J. Arabshahi、Jóhannes Reynisson、Christian G. Hartinger、Błażej Rychlik、Damian Plażuk

  DOI：10.1039/d1dt03553c

  日期：——

  strategy, we designed ferrocenyl analogs of monastrol – the first low molecular weight kinesin spindle protein (KSP) inhibitor. The obtained compounds showed low micromolar antiproliferative activity towards a panel of sensitive and ABC-overexpressing cancer cells. Most cytotoxic compounds exhibited also higher KSP modulatory activity and ability for ROS generation compared to monastrol. The increased

  将二茂铁基部分掺入生物活性分子可显着改变所得缀合物的活性。通过应用这种策略，我们设计了 monastrol 的二茂铁类似物——第一个低分子量驱动蛋白纺锤体蛋白 (KSP) 抑制剂。获得的化合物对一组敏感的和过度表达 ABC 的癌细胞显示出低微摩尔抗增殖活性。与 monastrol 相比，大多数细胞毒性化合物还表现出更高的 KSP 调节活性和产生 ROS 的能力。所研究化合物的生物活性增加可归因于二茂铁基团的存在。
• Indium(III) halides-catalyzed preparation of ferrocene-dihydropyrimidinones
  作者：Nan-Yan Fu、Yao-Feng Yuan、Mei-Li Pang、Ji-Tao Wang、Clovis Peppe

  DOI：10.1016/s0022-328x(03)00139-6

  日期：2003.4

  Indium(III) halides (chloride and bromide) catalyse the three-component Biginelli coupling of ferrocenyl-1,3-diketones, aldehydes and urea (or thiourea) to give 5-ferrocenoyl-3,4-dihydropyrimidinones. 4-Ferrocenyl-3,4-dihydropyrimidinones were obtained from alkyl-acetoacetates, formylferrocene and urea. The tricyclic compound, 13-ferrocenecarbonyl-9-methyl-11-oxo-8-oxa-10,12-diazatricyclo [7.3.1.0(2.7)] trideca-2,4-6-triene, was synthesized from 1-ferrocenyl-1,3-butanedione, salicilaldehyde and urea. (C) 2003 Elsevier Science B.V. All rights reserved.