ethyl 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate | 101852-97-5

• 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: ethyl 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
• 英文别名: Ethyl 3-(5-methyl-2,4-dioxopyrimidin-1-yl)propanoate
• CAS: 101852-97-5
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: HLCZCOBLTVDZNE-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C(Solv: ethanol (64-17-5))
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate 在 4-二甲氨基吡啶 、 hydrazine hydrate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-(cyclohexylmethyl)-3,5-dimethyl-N'-(3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoyl)benzohydrazide
  参考文献：
  名称：

  Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist

  摘要：

  Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 mu g/mL. This compound also caused malformation of molting larvae and adults. Compound 2h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.010
• 作为产物：
  描述：

  胸腺嘧啶 、 丙烯酸乙酯 在 三乙烯二胺 、 四丁基溴化铵 作用下， 反应 0.1h， 以78%的产率得到ethyl 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
  参考文献：
  名称：

  微波辅助迈克尔加成一些嘧啶和嘌呤核碱基与 α,β-不饱和酯：快速进入碳环核苷合成

  摘要：

  描述了在四丁基溴化铵 (TBAB) 和 DABCO 存在下，通过微波辅助迈克尔加成各种核碱基到 α,β-不饱和酯上合成一些碳环核苷的有效程序。使用这种方法，一些嘧啶和嘌呤核碱基已经以中等至高产率和短反应时间进行区域选择性烷基化。

  DOI：

  10.1055/s-2004-834950

文献信息

• Alkaline Protease from<i>Bacillus subtilis</i>Catalyzed Michael Addition of Pyrimidine Derivatives to α,β-Ethylenic Compounds in Organic Media
  作者：Xian-Fu Lin、Ying Cai、Xiao-Feng Sun、Na Wang

  DOI：10.1055/s-2004-815982

  日期：——

  Michael addition reactions of pyrimidine derivatives to α,β-ethylenic compounds were catalyzed by an alkaline protease from Bacillus subtilis in DMSO at 50 °C. The structure of adducts were determined by 1R, NMR and MS. The yields were from 20% to 84%.

  嘧啶衍生物与 α,β-烯属化合物的迈克尔加成反应由来自枯草芽孢杆菌的碱性蛋白酶在 50°C 的 DMSO 中催化。加合物的结构通过1R、NMR和MS确定。产率为20%至84%。
• Facile Aza-Michael Additions of Uracil Derivatives to Acrylates
  作者：Shuguang Zhou、Mingxia Xu、Siyu Ye、Dashuai Li、Jing Xu、Pei Mao、Jing Xiong

  DOI：10.3184/174751912x13282923623804

  日期：2012.2

  24 Aza-Michael adducts were synthesised in moderate to excellent yields by the addition of 5-substituted uracils to acrylates with ethylamine as a catalyst. Many of the adducts were obtained in almost quantitive yield without column chromatography. The procedure provideded an efficient approach to the synthesis of N-1 uracil adducts using acrylates as acceptors. The structures of the compounds were determined by ¹H NMR, ¹³C NMR, mass spectra and X-ray crystallography analyses. The uracil unit is present in DNA and related natural products and has a broad spectrum of biological activity.

  以乙胺为催化剂，将 5-取代的尿嘧啶加到丙烯酸酯中，合成了 24 种 Aza-Michael 加合物，收率从中等到极好。许多加合物无需柱层析即可获得几乎定量的产率。该方法提供了一种以丙烯酸酯为受体合成 N-1 尿嘧啶加合物的有效途径。化合物的结构是通过 1H NMR、13C NMR、质谱和 X 射线晶体学分析确定的。尿嘧啶单元存在于 DNA 和相关天然产物中，具有广泛的生物活性。
• Zinc oxide-tetrabutylammonium bromide tandem as a highly efficient, green, and reusable catalyst for the Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters under solvent-free conditions
  作者：Abdolkarim Zare、Alireza Hasaninejad、Mohammad Hassan Beyzavi、Abolfath Parhami、Ahmad Reza Moosavi Zare、Ali Khalafi-Nezhad、Hashem Sharghi

  DOI：10.1139/v08-022

  日期：2008.4.1

  An efficient procedure for the synthesis of carboacyclic nucleosides via microwave-assisted Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters in the presence of cataly...

  在催化剂存在下，通过嘧啶和嘌呤核碱基与 α,β-不饱和酯的微波辅助迈克尔加成合成碳环核苷的有效方法...
• Spectroscopic Evaluation of Novel Adenine/Thymine-Conjugated Naphthalenediimides: Preference of Adenine-Adenine over Thymine-Thymine Intermolecular Hydrogen Bonding in Adenine- and Thymine-Functionalized Naphthalenediimides
  作者：Digambara Patra、Nadine Al Homsi、Sara Jaafar、Zeina Neouchy、Jomana Elaridi、Ali Koubeissi、Kamal H. Bouhadir

  DOI：10.1007/s10895-018-02340-6

  日期：2019.1

  (adenine/thymine)-conjugated naphthalenediimides (NDIs), namely, NDI-AA, NDI-TT, and NDI-AT have been successfully achieved. NDI-AA, NDI-TT and NDI-AT have similar absorption in the 300–400 nm region. The effect of solvent on the absorption spectrum indicates aggregation, either through intermolecular π-σ interaction among the main chromophore or through intermolecular hydrogen bonding between adenine and adenine group

  已经成功地实现了新型核碱基（腺嘌呤/胸腺嘧啶）-共轭萘二酰亚胺（NDI-AA），NDI-AA和NDI-AT的合成和光谱表征。NDI-AA，NDI-TT和NDI-AT在300-400 nm区域具有相似的吸收。溶剂对吸收光谱的影响表明是通过主要生色团之间的分子间π-σ相互作用或通过腺嘌呤和腺嘌呤基团之间的分子间氢键键合引起的聚集。加水无助于胸腺嘧啶-胸腺嘧啶之间的氢键形成，而是增加溶剂的极性会促进NDI-TT之间的π-σ相互作用。随着温度的升高，NDI-TT的光谱没有变化，这表明氢键在NDI-TT中没有发挥关键作用。对NDI-AA的荧光研究还建立了准分子形成以及基态聚集。随着溶剂混合物中水含量的增加，根据早期结果，由于腺嘌呤-腺嘌呤氢键，不鼓励NDI-AA聚集。同时，NDI-TT发射光谱不会移到蓝色区域，并且535 nm附近的峰强度增加，但以411 nm的荧光为代价。因此，由于胸腺嘧啶-胸腺嘧
• KF/Al₂O₃as a Highly Efficient, Green, Heterogeneous, and Reusable Catalytic System for the Solvent-Free Synthesis of Carboacyclic Nucleosides via Michael Addition Reaction
  作者：Abdolkarim Zare、Alireza Hasaninejad、Mohammad Hassan Beyzavi、Ahmad Reza Moosavi Zare、Ali Khalafi-Nezhad、Fatemeh Asadi、Leila Baramaki、Sedigheh Jomhori-Angali、Rokhsareh Ghaleh-Golabi

  DOI：10.1080/00397910802369711

  日期：2008.12.16

  Abstract KF/Al2O3 acts as an efficient catalytic system for the synthesis of carboacyclic nucleosides via Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters under solvent-free and microwave conditions. Using this method, the title compounds are produced in good to excellent yields and short reaction times.

  摘要 KF/Al2O3 是一种有效的催化体系，可在无溶剂和微波条件下通过嘧啶和嘌呤核碱基与 α,β-不饱和酯的迈克尔加成反应合成碳环核苷。使用这种方法，可以以良好到极好的收率和较短的反应时间生产标题化合物。