3-(2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-yl)propionic acid butyl ester

• 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: 3-(2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-yl)propionic acid butyl ester
• 英文别名: 3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid butyl ester；butyl 3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate；n-butyl 3-(1'-uracil)propionate；Butyl 3-(2,4-dioxopyrimidin-1-yl)propanoate
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: XMVZVTXJCUIOSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 尿嘧啶 在 lipozyme Thermomyces lanuginosus IM 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以72%的产率得到3-(2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-yl)propionic acid butyl ester
  参考文献：
  名称：

  在连续流动的微反应器中 ，脂肪酶TL IM催化来自羊毛嗜热霉菌的嘧啶嘧啶衍生物与丙烯酸酯的迈克尔加成反应†

  摘要：

  描述了在连续流微反应器中脂肪酶催化的嘧啶衍生物的迈克尔加成到丙烯酸酯。还研究了迈克尔受体和相应供体的结构对酶促加成的影响。该方法的重要特征包括温和的反应条件，短的反应时间（30分钟）和高收率。

  DOI：

  10.1039/c3ra47470d

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...
• 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。
• Microwave-Assisted Michael Addition of Some Pyrimidine and Purine Nucleobases with α,β-Unsaturated Esters: A Rapid Entry into Carboacyclic Nucleoside Synthesis
  作者：A. Khalafi-Nezhad、A. Zarea、M. N. Soltani Rad、B. Mokhtari、A. Parhami

  DOI：10.1055/s-2004-834950

  日期：——

  An efficient procedure for the synthesis of some carboacyclic nucleosides via microwave-assisted Michael addition of various nucleobases to α,β-unsaturated esters in the presence of tetrabutylammonium bromide (TBAB) and DABCO is described. Using this method, some pyrimidine and purine nucleobases have been alkylated regioselectively in moderate to high yields and short reaction time.

  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。