5-(4-formylphenyl)-2'-deoxyuridine | 847659-07-8

• 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-formylphenyl)-2'-deoxyuridine
• 英文别名: 4-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]benzaldehyde
• CAS: 847659-07-8
• 化学式: C₁₆H₁₆N₂O₆
• 分子量: 332.313
• InChiKey: ITKVIZZBUXFVMC-BFHYXJOUSA-N

物化性质

• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-formylphenyl)-2'-deoxyuridine 在 吡啶 、 咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(5-{4-[1,3-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,5,5-tetramethyl-imidazolidin-2-yl]-phenyl}-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis and ESR studies of nitronyl nitroxide-tethered oligodeoxynucleotides

  摘要：

  We report oil the development of a nucleoside labeled with a nitronyl nitroxide group, U-NN, and the synthesis of oligodeoxynucleotides containing U-NN. The spin signals of U-NN. containing oligodeoxynucleotides varied with the degree of hybridization of the complementary strand and the distance between nitronyl nitroxide spins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.012
• 作为产物：
  描述：

  4-甲酰基苯硼酸 、 碘苷 在 [Pd(succinimidate)2(1,3,5-triaza-7-phosphaadamantane)2] 、 三乙胺 作用下， 以 水 为溶剂， 反应 6.08h， 以85%的产率得到5-(4-formylphenyl)-2'-deoxyuridine
  参考文献：
  名称：

  水溶性Pd-酰亚胺酸盐配合物：通过Pd催化交叉偶联合成化学修饰的核苷的广泛应用催化剂

  摘要：

  已采用由水溶性Pd-亚氨酸盐络合物组成的广泛适用的催化剂体系，以在温和条件下将水中的四个不同核苷进行Suzuki-Miyaura交叉偶联。催化剂体系的有效性质也使其可用于开发微波辅助规程，以加快催化反应的速度。初步的机理研究，借助催化剂毒性试验和使用电喷雾电离光谱仪进行的化学计量测试，揭示了可能存在同位催化剂体系。

  DOI：

  10.1021/acs.joc.5b02475

文献信息

• Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids
  作者：Hans-Achim Wagenknecht、Thomas Ehrenschwender

  DOI：10.1055/s-0028-1083206

  日期：2008.11

  BODIPY-modified nucleosides that contain the fluorophore attached to the 5-position of uridine via a short phenylene bridge have been prepared and characterized by optical spectroscopy and by electrochemistry. The target compounds were synthesized using a Pd-catalyzed cross-coupling of 4-formyl­-phenylboronic acid to 5-iodo-2′-desoxyuridine, followed by acid-catalyzed formation of the BODIPY chromophore. The weakly electron-donating ethyl substituents in positions 2 and 6 of the BODIPY­ dye, shift both the absorption and emission properties of the corresponding modified uridines bathochromically and alter their redox properties. In contrast, exchange of the fluoro ligands at the boron center of the chromophores by methoxy groups does not change the optical properties but increases the electron-rich character of the BODIPY-modified uridines significantly.

  已经合成并通过光谱学和电化学对改性BODIPY核苷进行表征，这些核苷的荧光团通过短的苯撑桥连接在尿苷的5位。目标化合物是通过钯催化的交叉偶联反应将4-甲酰基苯硼酸与5-碘-2′-去氧尿苷合成的，随后通过酸催化形成BODIPY色素。BODIPY染料在2位和6位的弱电子给体乙基取代基使得相应改性尿苷的吸收和发射特性都向红外区移动，并改变其氧化还原特性。相比之下，色素中心的氟配体被甲氧基取代，并不会改变光学性质，但显著增强了BODIPY改性尿苷的电子富集特性。
• 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。
• 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
• 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。
• Nucleotide insertion and bypass synthesis of pyrene- and BODIPY-modified oligonucleotides by DNA polymerases
  作者：Claudia Wanninger-Weiß、Francesca Di Pasquale、Thomas Ehrenschwender、Andreas Marx、Hans-Achim Wagenknecht

  DOI：10.1039/b718002k

  日期：——

  The chromophores pyrene and bordipyrromethenylbenzene directly linked to the 5-position of uridine are tolerated and recognized as thymine derivatives by DNA polymerases in primer extension experiments.

  在引物延伸实验中，与尿苷的 5 位直接相连的发色团芘和溴代吡咯并苯（bordipyrromethenylbenzene）可被 DNA 聚合酶识别为胸腺嘧啶衍生物。