1-allyl-5-iodo-1H-pyrimidine-2,4-dione | 403668-60-0

• 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-allyl-5-iodo-1H-pyrimidine-2,4-dione
• 英文别名: 5-Iodo-1-prop-2-enylpyrimidine-2,4-dione
• CAS: 403668-60-0
• 化学式: C₇H₇IN₂O₂
• 分子量: 278.049
• InChiKey: NXPZASRPXDJUEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-5-iodo-1H-pyrimidine-2,4-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium diacetate 、 三苯胂 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-[(E)-4,5-dihydroxy-2-pentenyl]-5-(2-thienyl)-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

  摘要：

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.019
• 作为产物：
  描述：

  乙酸烯丙酯 、 5-碘尿嘧啶 在 四(三苯基膦)钯 1,1'-双(二苯基膦)二茂铁 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到1-allyl-5-iodo-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  通过钯介导的烯丙基烷基化和交叉复分解获得无环核苷的新途径

  摘要：

  描述了通过钯催化的烯丙基烷基化和基于钌的交叉复分解的组合来合成E-不饱和无环核苷的方法。这种方法为新的核苷类似物提供了简洁，有效和可靠的途径。

  DOI：

  10.1016/j.tetlet.2003.10.029

文献信息

• A new route to acyclic nucleosides via palladium-mediated allylic alkylation and cross-metathesis
  作者：Franck Amblard、Steven P. Nolan、Isabelle Gillaizeau、Luigi A. Agrofoglio

  DOI：10.1016/j.tetlet.2003.10.029

  日期：2003.12

  A method for the syntheses of E-unsaturated acyclic nucleosides via a combination of palladium-catalyzed allylic alkylation and ruthenium-based cross metathesis is described. This approach provides a concise, efficient and reliable route to new nucleoside analogues.

  描述了通过钯催化的烯丙基烷基化和基于钌的交叉复分解的组合来合成E-不饱和无环核苷的方法。这种方法为新的核苷类似物提供了简洁，有效和可靠的途径。
• The Convenient Synthesis of Unsaturated Nucleoside Analogues in Water under Microwave Irradiation
  作者：Ran Xia、Li-Ping Sun

  DOI：10.1080/15257770.2015.1114129

  日期：2016.2

  A convenient method for the regioselective synthesis of unsaturated nucleoside analogs in water under microwave irradiation was developed. All pyrimidine and purine nucleoside derivatives were exclusively alkylated at N1 and N9 respectively in good to excellent yields. In addition, this system could tolerate a broad range of functional groups, such as chloro, bromo, iodo, alkyl, amino, and hydroxyl

  开发了一种方便的微波辐射下水中不饱和核苷类似物区域选择性合成的方法。所有嘧啶和嘌呤核苷衍生物分别分别在N1和N9处烷基化，收率良好至极佳。另外，该系统可以耐受广泛的官能团，例如氯，溴，碘，烷基，氨基和羟基。更重要的是，反应规模可以扩大到50 mmol，这使该路线对工业应用具有吸引力。
• Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies
  作者：Franck Amblard、Steven P. Nolan、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/j.tet.2004.11.019

  日期：2005.1

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.