N¹-[(E)-3-(dihydroxyphosphinyl)-prop-2-enyl]-5-(phenylthio)uracil | 1023339-93-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N¹-[(E)-3-(dihydroxyphosphinyl)-prop-2-enyl]-5-(phenylthio)uracil
• 英文别名: [(E)-3-(2,4-dioxo-5-phenylsulfanylpyrimidin-1-yl)prop-1-enyl]phosphonic acid
• CAS: 1023339-93-6
• 化学式: C₁₃H₁₃N₂O₅PS
• 分子量: 340.296
• InChiKey: PQDCGUNDIQPFHW-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N1-[(E)-3-(diethoxyphosphinyl)-prop-2-enyl]-5-(phenylthio)uracil 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88%的产率得到N¹-[(E)-3-(dihydroxyphosphinyl)-prop-2-enyl]-5-(phenylthio)uracil
  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

• 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.