5-(4-acetylphenyl)-2'-deoxyuridine | 1373213-44-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(4-acetylphenyl)-2'-deoxyuridine
• 英文别名: 5-(4-acetylphenyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1373213-44-5
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: GSVYGYUHHORWPX-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘苷 、 4-乙酰基苯硼酸 在 sodium tetrachloropalladate 、 trisodium tris(3-sulfophenyl)phosphine 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以70%的产率得到5-(4-acetylphenyl)-2'-deoxyuridine
  参考文献：
  名称：

  铃木-宫浦交叉偶联在水中高效合成C-5取代的2'-脱氧尿苷

  摘要：

  已经建立了使用钯催化的水中Suzuki-Miyaura交叉偶联反应提供一系列C-5-取代的2'-脱氧尿苷衍生物的有效方案。从2'-脱氧尿苷衍生物开始，以良好的收率获得了目标核苷类似物，钯负载量低，而没有保护糖基部分的任何羟基。 交叉偶联-铃木宫浦-核苷-绿色化学

  DOI：

  10.1055/s-0031-1289709

文献信息

• Improved microwave-assisted ligand-free Suzuki–Miyaura cross-coupling of 5-iodo-2′-deoxyuridine in pure water
  作者：Shawn Gallagher-Duval、Gwénaëlle Hervé、Guillaume Sartori、Gérald Enderlin、Christophe Len

  DOI：10.1039/c3nj00174a

  日期：——

  A facile and efficient methodology for direct synthesis of 5-aryl-2′-deoxyuridines was developed through ligand-free Suzuki–Miyaura cross-coupling reactions starting from totally deprotected 5-iodo-2′-deoxyuridine and various boronic acids. Reactions were performed, in pure water, in the presence of very low loading of palladium either by classical thermal heating or with the assistance of microwave irradiation yielding 5-arylated uridine derivatives in moderate to good yields within short reaction times.

  通过无配体铃木-宫浦交叉偶联反应，从完全脱保护的5-碘-2-脱氧尿苷和各种硼酸出发，开发了一种简单有效的5-芳基-2-脱氧尿苷直接合成方法。在纯水中，通过经典的热加热或在微波辐射的辅助下，在极低钯负载的情况下进行反应，在较短的反应时间内，以中等至良好的产率生成5-芳基尿苷衍生物。
• Efficient Synthesis of Unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura Reaction in Aqueous Media
  作者：Nathalie Fresneau、Marie-Aude Hiebel、Luigi Agrofoglio、Sabine Berteina-Raboin

  DOI：10.3390/molecules171214409

  日期：——

  Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligands, since palladium acetate and triphenylphosphine afforded the expected products in moderate to good yields.

  继我们之前在水溶液条件下通过无害环境的一锅 Sonogashira-环化方案获得取代的呋喃嘧啶核苷的研究成果之后，我们在此研究了在相同介质中使用普通催化剂体系，避免使用外来配体，在未受保护的 2'-脱氧尿苷的 C5 位上进行芳基和杂芳基衍生物的 Suzuki-Miyaura 交叉偶联反应，因为醋酸钯和三苯基膦能以中等至良好的收率提供预期产物。
• New, Efficient Approach for the Ligand-Free Suzuki–Miyaura Reaction of 5-Iodo-2′-deoxyuridine in Water
  作者：Christophe Len、Guillaume Sartori、Gwénaëlle Hervé、Gérald Enderlin

  DOI：10.1055/s-0032-1317847

  日期：——

  A series of 5-aryl-2'-deoxyuridines was prepared, using ligandless Suzuki-Miyaura cross-coupling reactions in neat water, starting from 5-iodo-2'-deoxyuridine as totally deprotected starting material. This ligand-free process gave good to high isolated yields within short reaction times and with low loadings of palladium.
• Highly Effective Synthesis of C-5-Substituted 2′-Deoxyuridine Using Suzuki-Miyaura Cross-Coupling in Water
  作者：Christophe Len、Guillaume Sartori、Gérald Enderlin、Gwénaelle Hervé

  DOI：10.1055/s-0031-1289709

  日期：2012.3

  C-5-substituted 2′-deoxyuridine derivatives using a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction in water has been established. Starting from 2′-deoxyuridine derivatives, the target nucleoside analogues were obtained in good yields with low levels of palladium loading without protection of any hydroxyl group of the glycone moiety. cross-coupling - Suzuki-Miyaura - nucleosides - green chemistry

  已经建立了使用钯催化的水中Suzuki-Miyaura交叉偶联反应提供一系列C-5-取代的2'-脱氧尿苷衍生物的有效方案。从2'-脱氧尿苷衍生物开始，以良好的收率获得了目标核苷类似物，钯负载量低，而没有保护糖基部分的任何羟基。 交叉偶联-铃木宫浦-核苷-绿色化学