1-(2-cyanoethyl)thymine | 6388-18-7

• 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: 1-(2-cyanoethyl)thymine
• 英文别名: 3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)yl)propanenitrile；3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanenitrile；1-(2-Cyan-ethyl)-thymin；1-(2-Cyanoaethyl)thymin；3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionitrile；β-(Thyminyl-N³)-propionitril；Uracilyl-propionitril；3-(5-methyl-2,4-dioxopyrimidin-1-yl)propanenitrile
• CAS: 6388-18-7
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: CKLUUTYIHZFEPA-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-cyanoethyl)thymine 在 palladium on activated charcoal ammonium formate 作用下， 以 正丁醇 为溶剂， 反应 120.0h， 以27%的产率得到3-(thymine-1-yl)propylamine
  参考文献：
  名称：

  Boncel; Walczak, Polish Journal of Chemistry, 2007, vol. 81, # 12, p. 2151 - 2156

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1-thyminyl)propanoic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 1-(2-cyanoethyl)thymine
  参考文献：
  名称：

  N-1和N-3尿嘧啶加合物的区域选择性合成中的Michael与Michael逆反应

  摘要：

  通过控制5-取代的尿嘧啶衍生物在碱催化的迈克尔型加成反应中的温度或反应时间，我们能够使用丙烯酸甲酯和丙烯腈作为受体合成N-1或N-3尿嘧啶加合物。使用1 H NMR光谱研究确定了这种化学不等价的机理。研究表明，无论所用碱类（TEA，DBU）如何，在动力学控制条件下均可形成N-1加合物。反过来，N-3加合物的合成是从最初形成的N-1，N-3二加合物通过逆迈克尔反应进行的，该反应在升高的温度或延长的反应时间中起主导作用。

  DOI：

  10.1016/j.tet.2010.08.059

文献信息

• Michael addition of pyrimidine derivatives with acrylates catalyzed by lipase TL IM from Thermomyces lanuginosus in a continuous-flow microreactor
  作者：Li-Hua Du、Hui-Min Ling、Xi-Ping Luo

  DOI：10.1039/c3ra47470d

  日期：——

  Lipase-catalyzed Michael addition of pyrimidine derivatives to acrylates in a continuous-flow microreactor is described. The influence of the structure of the Michael acceptor and the corresponding donor on the enzymatic addition was also investigated. The important features of this method include mild reaction conditions, short reaction times (30 min) and high yields.

  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。
• Customizable and Regioselective One‐Pot N−H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications
  作者：Djenisa H. A. Rocha、Carmen M. Machado、Vera Sousa、Cristiana F. V. Sousa、Vera L. M. Silva、Artur M. S. Silva、João Borges、João F. Mano

  DOI：10.1002/ejoc.202100786

  日期：2021.8.20

  synthetic procedures for producing a library of nucleobase derivatives enlisted with reactive functional groups for bioconjugation and cross-linking reactions with other biomolecules are reported. The nucleobase derivatives bearing either N-alkyl, N-propanenitrile, N-allyl or N-propargyl terminals are non-cytotoxic, denoting great promise for biomedical applications.

  一锅合成程序用于生产核碱基衍生物库，该库具有反应性官能团，用于与其他生物分子进行生物共轭和交联反应。带有N - 烷基、N - 丙腈、N - 烯丙基或N -炔丙基末端的核碱基衍生物是无细胞毒性的，在生物医学应用方面具有广阔的前景。
• Microwave-Promoted Michael Addition in Neat Water: A Rapid, Efficient and Green Method for the Preparation of Acyclic Nucleosides
  作者：Gui-Rong Qu、Hai-Ming Guo、Zhi-Guang Zhang、Ming-Wei Geng、Ran Xia、Lin Zhao

  DOI：10.1055/s-2007-970772

  日期：2007.3

  Syntheses of acyclic nucleosides were achieved in water with the aid of microwave irradiation, providing a rapid, efficient and convenient method for the preparation of acyclic nucleosides in high yields.

  在微波辐射的帮助下，实现了在水中合成无环核苷的过程，提供了一种快速、高效和便利的无环核苷高产量制备方法。
• Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues
  作者：Slawomir Boncel、Krzysztof Walczak

  DOI：10.1080/15257770902736467

  日期：2009.3.11

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.
• Crippa, Sergio; Di Gennaro, Patrizia; Lucini, Ruggero, Gazzetta Chimica Italiana, 1993, vol. 123, # 4, p. 197 - 203
  作者：Crippa, Sergio、Di Gennaro, Patrizia、Lucini, Ruggero、Orlandi, Marco、Rindone, Bruno

  DOI：——

  日期：——