N¹-[(E)-3-(diethoxyphosphinyl)-prop-2-enyl]-5-phenyluracil | 1023339-63-0

• 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: N¹-[(E)-3-(diethoxyphosphinyl)-prop-2-enyl]-5-phenyluracil
• 英文别名: 1-[(E)-3-[diethoxy(oxido)phosphaniumyl]prop-2-enyl]-5-phenylpyrimidine-2,4-dione
• CAS: 1023339-63-0
• 化学式: C₁₇H₂₁N₂O₅P
• 分子量: 364.338
• InChiKey: SBRUYYPKUXHKBZ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N¹-[(E)-3-(diethoxyphosphinyl)-prop-2-enyl]-5-phenyluracil 在 三甲基溴硅烷 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以97%的产率得到N¹-[(E)-3-(dihydroxyphosphinyl)-prop-2-enyl]-5-phenyluracil
  参考文献：
  名称：

  Preparation of acyclo nucleoside phosphonate analogues based on cross-metathesis

  摘要：

  In our on-going program targeting anti-pox activity, we report here the synthesis of hitherto unknown acyclic nucleoside phosphonates using olefin cross-metathesis (CM) as a key assembly step. Modification at the C-5 position of the uracil moiety was performed under optimized Pd(0)-catalyzed Stille cross-coupling conditions. None of the obtained compounds were active against poxviruses, nor do they exhibit any toxicity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.140
• 作为产物：
  描述：

  N1-crotyl-5-phenyluracil 、 乙烯基磷酸二乙酯 在 (1,3-dimesityl-4-imidazolin-2-ylidene)(PhCH=)RuCl₂(PCy₃) 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以67%的产率得到N¹-[(E)-3-(diethoxyphosphinyl)-prop-2-enyl]-5-phenyluracil
  参考文献：
  名称：

  Preparation of acyclo nucleoside phosphonate analogues based on cross-metathesis

  摘要：

  In our on-going program targeting anti-pox activity, we report here the synthesis of hitherto unknown acyclic nucleoside phosphonates using olefin cross-metathesis (CM) as a key assembly step. Modification at the C-5 position of the uracil moiety was performed under optimized Pd(0)-catalyzed Stille cross-coupling conditions. None of the obtained compounds were active against poxviruses, nor do they exhibit any toxicity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.140

文献信息

• Cross-Metathesis Mediated Synthesis of New Acyclic Nucleoside Phosphonates
  作者：Vincent Roy、Hiroki Kumamoto、Sabine Berteina-Raboin、Steven P. Nolan、Dimitri Topalis、Dominique Deville-Bonne、Jan Balzarini、Johan Neyts、Gracelia Andrei、Robert Snoeck、Luigi A. Agrofoglio

  DOI：10.1080/15257770701534196

  日期：2007.11.26

  catalysts which combine high stability and broad functional group compatibility, olefin metathesis is now routinely integrated in various syntheses. We will report here the overwhelming power and scope of cross-metathesis in the area of new acyclic nucleoside phosphonates. Scope and limitations of this approach, and especially the E/Z stereocontrol, are discussed on selected examples from our drug discovery

  由于结合了高稳定性和广泛的官能团相容性的明确定义的钌复分解催化剂的商业可得性，烯烃复分解现在已常规地整合到各种合成中。我们将在这里报告新的无环核苷膦酸酯领域交叉复分解的压倒性能力和范围。我们从药物研发小组的精选实例中讨论了这种方法的范围和局限性，尤其是E / Z立体控制。
• Preparation of acyclo nucleoside phosphonate analogues based on cross-metathesis
  作者：Hiroki Kumamoto、Dimitri Topalis、Julie Broggi、Ugo Pradère、Vincent Roy、Sabine Berteina-Raboin、Steven P. Nolan、Dominique Deville-Bonne、Graciela Andrei、Robert Snoeck、Daniel Garin、Jean-Marc Crance、Luigi A. Agrofoglio

  DOI：10.1016/j.tet.2008.01.140

  日期：2008.4

  In our on-going program targeting anti-pox activity, we report here the synthesis of hitherto unknown acyclic nucleoside phosphonates using olefin cross-metathesis (CM) as a key assembly step. Modification at the C-5 position of the uracil moiety was performed under optimized Pd(0)-catalyzed Stille cross-coupling conditions. None of the obtained compounds were active against poxviruses, nor do they exhibit any toxicity. (c) 2008 Elsevier Ltd. All rights reserved.