2-methylthio-4-diethylamino-6-vinyl pyrimidine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylthio-4-diethylamino-6-vinyl pyrimidine
• 英文别名: 6-ethenyl-N,N-diethyl-2-methylsulfanylpyrimidin-4-amine
• 化学式: C₁₁H₁₇N₃S
• 分子量: 223.342
• InChiKey: AUOKPZCLELUQIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-[2-(diethylamino)ethyl]-2-methylsulfanyl-1H-pyrimidin-6-one 在 sodium hydride 、 正丁醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以45%的产率得到2-methylthio-4-diethylamino-6-vinyl pyrimidine
  参考文献：
  名称：

  在C-6侧链上带有二乙氨基部分的2-甲氧基-和2-甲硫基-4（3 ）-嘧啶酮上的意外且有效的直接亲核C-4羟基取代

  摘要：

  报道了在C-6侧链上带有二乙氨基部分的2-甲氧基-和2-甲硫基-4（3H）-嘧啶酮上的烷醇钠意外和有效的直接亲核C-4羟基（氧代）取代。还报道了空前的串联C-6侧链霍夫曼样消除/ C-4嘧啶酮取代。这为合成新的C-6乙烯基胞嘧啶衍生物提供了一个很好的方法。

  DOI：

  10.1016/s0040-4039(97)10159-9

文献信息

• A new and efficient synthesis of substituted 6-[(2′-Dialkylamino)ethyl] pyrimidine and 4- N,N -Dialkyl-6-vinyl-cytosine derivatives and evaluation of their anti-Rubella activity
  作者：Raffaele Saladino、Umberto Ciambecchini、Giovanni Maga、Paola Mastromarino、Cinzia Conti、Maurizio Botta

  DOI：10.1016/s0968-0896(02)00077-9

  日期：2002.7

  New 6[(2'-dialkylamino)ethyl]-4(3H)-pyrimidinones were prepared by a multistep procedure starting from acetone dicarboxylic acid diethyl ester and urea derivatives. These compounds were used as starting materials to obtain 4-N,N-dialkyl-6-vinyl-pyrimidine derivatives by an unprecedented tandem C-6 side chain Hofmann-like elimination/C-4 pyrimidinone substitution. Among the new derivatives obtained, various compounds show anti-Rubella activity. The inhibition of HIV-1 Reverse Transcriptases (RT), from both wild type and modified viruses, is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain
  作者：Maurizio Botta、Francesca Occhionero、Raffaele Saladino、Claudia Crestini、Rosario Nicoletti

  DOI：10.1016/s0040-4039(97)10159-9

  日期：1997.11

  The unexpected and efficient direct nucleophilic C-4 hydroxy (oxo) substitution by sodium alkoxides on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain is reported. An unprecedented tandem C-6 side chain Hofmann-like elimination /C-4 pyrimidinone substitution is also reported. This provides a good method for the synthesis of new C-6 vinyl cytosine

  报道了在C-6侧链上带有二乙氨基部分的2-甲氧基-和2-甲硫基-4（3H）-嘧啶酮上的烷醇钠意外和有效的直接亲核C-4羟基（氧代）取代。还报道了空前的串联C-6侧链霍夫曼样消除/ C-4嘧啶酮取代。这为合成新的C-6乙烯基胞嘧啶衍生物提供了一个很好的方法。