N-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)formamidine | 176240-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)formamidine
• 英文别名: Ethyl 2-amino-2-[(2-methylpropan-2-yl)oxycarbonylimino]acetate；ethyl 2-amino-2-[(2-methylpropan-2-yl)oxycarbonylimino]acetate
• CAS: 176240-37-2
• 化学式: C₉H₁₆N₂O₄
• 分子量: 216.237
• InChiKey: XQPCIANGWBSMTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)formamidine 在 吡啶 、 双(对硝基苯基)磷酸酯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 78.0h， 生成 ethyl 5-hydroxymethyl-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  芳基乙烯基三唑核苷的替代途径

  摘要：

  开发了合成芳基乙烯基利巴韦林类似物的新途径，这不仅使在乙烯基键处获得反式-而且还获得顺式-异构体成为可能。通过这种途径，合成了八个利巴韦林5-芳基乙烯基类似物，并评估了它们的抗病毒活性。

  DOI：

  10.1016/j.bmcl.2016.05.072
• 作为产物：
  描述：

  硫代草氨酸乙酯 、 肼基甲酸叔丁酯 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到N-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)formamidine
  参考文献：
  名称：

  芳基乙烯基三唑核苷的替代途径

  摘要：

  开发了合成芳基乙烯基利巴韦林类似物的新途径，这不仅使在乙烯基键处获得反式-而且还获得顺式-异构体成为可能。通过这种途径，合成了八个利巴韦林5-芳基乙烯基类似物，并评估了它们的抗病毒活性。

  DOI：

  10.1016/j.bmcl.2016.05.072

文献信息

• 1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹
  作者：Angel Guzmán、Moisés Romero、Francisco X. Talamás、Rene Villena、Robert Greenhouse、Joseph M. Muchowski

  DOI：10.1021/jo952106w

  日期：1996.1.1

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.
• An alternative route to the arylvinyltriazole nucleosides
  作者：Mikhail V. Chudinov、Alexander N. Prutkov、Andrey V. Matveev、Lyubov E. Grebenkina、Irina D. Konstantinova、Yulia V. Berezovskaya

  DOI：10.1016/j.bmcl.2016.05.072

  日期：2016.7

  A new pathway to synthesis of arylvinyl ribavirin analogues is developed which makes it possible to obtain not only trans- but also cis-isomers at vinyl bond. By this route eight ribavirin 5-arylvinyl analogues are synthesized and their antiviral activity is evaluated.

  开发了合成芳基乙烯基利巴韦林类似物的新途径，这不仅使在乙烯基键处获得反式-而且还获得顺式-异构体成为可能。通过这种途径，合成了八个利巴韦林5-芳基乙烯基类似物，并评估了它们的抗病毒活性。