5-phenyluridine | 75759-66-9

• 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-phenyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-phenylpyrimidine-2,4-dione
• CAS: 75759-66-9
• 化学式: C₁₅H₁₆N₂O₆
• 分子量: 320.302
• InChiKey: VIVJVCKOJIDEPR-HKUMRIAESA-N

物化性质

• 熔点：
  181-182 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-iodo-2',3'-O isopropylidene-uridine 在 甲酸 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 5-phenyluridine
  参考文献：
  名称：

  用光化学方法简单合成荧光尿苷

  摘要：

  通过2'，3'-0-异亚丙基-5-碘尿苷与pyr的光反应制备了强荧光的5-吡啶基尿苷。通过类似的方法合成了尿嘧啶的几种荧光类似物。

  DOI：

  10.1016/s0040-4039(00)78614-x

文献信息

• Practical synthesis of 6-aryluridines via palladium(II) acetate catalyzed Suzuki–Miyaura cross-coupling reaction
  作者：Yu-Chiao Shih、Tun-Cheng Chien

  DOI：10.1016/j.tet.2011.03.051

  日期：2011.5

  Sugar-protected 6-halouridine derivatives underwent Suzuki–Miyaura cross-coupling reactions with arylboronic acids in the presence of palladium(II) acetate as a catalyst, triphenylphosphine as a ligand, and sodium carbonate as a base. This methodology is applicable to both the C5- and C6-position of uridine and provides a direct access for versatile uridine derivatives.

  在乙酸钯（II）作为催化剂，三苯基膦作为配体和碳酸钠作为碱的存在下，糖保护的6-卤代吡啶衍生物与芳基硼酸进行了Suzuki-Miyaura交叉偶联反应。该方法学适用于尿苷的C5和C6位置，并为通用尿苷衍生物提供了直接途径。
• Novel derivatives of UDP-glucose: concise synthesis and fluorescent properties
  作者：Thomas Pesnot、Gerd K. Wagner

  DOI：10.1039/b805216f

  日期：——

  A series of novel 5-substituted UDP-glucose derivatives with interesting fluorescent properties and potential applications as sensors for carbohydrate-active enzymes is reported. An efficient synthesis of the target molecules was developed, centred around the Suzuki–Miyaura reaction of (hetero)arylboronic acids with 5-iodo UDP-glucose. Interestingly, the optimised cross-coupling conditions could also be applied successfully to 5-bromo UMP, but not to 5-bromo UDP-glucose.

  报告了一系列具有有趣荧光特性和作为碳水化合物活性酶传感器潜在应用的新型5取代UDP-葡萄糖衍生物。开发了一种高效的目标分子的合成方法，主要围绕5-碘UDP-葡萄糖与(杂)芳基硼酸的铃木-宫浦反应进行。有趣的是，优化的交叉偶联条件同样成功应用于5-溴UMP，但不适用于5-溴UDP-葡萄糖。
• Analogues of uracil nucleosides with intrinsic fluorescence (NIF-analogues): synthesis and photophysical properties
  作者：Meirav Segal、Bilha Fischer

  DOI：10.1039/c1ob06536j

  日期：——

  were obtained from 5-I-uridine and the suitable boronic acid in a Sonogashira coupling reaction. The uracil fluorescent analogues proposed here were designed to satisfy the following requirements: a minimal chemical modification at a position not involved in base-pairing, resulting in relatively long absorption and emission wavelengths and high quantum yield. 5-((4-Methoxy-phenyl)-trans-vinyl)-2′-deoxy-uridine

  尿苷由于其量子产率极低，因此不能用作荧光探针。为了改善尿嘧啶的荧光特性，我们通过直接或通过烯基或炔基连接基团连接取代的芳香环来扩展荧光团，从而扩展了C5位置的天然发色团。尿嘧啶碱基的延伸是通过在Suzuki偶联条件下用适当的硼酸处理5-I-尿苷来实现的。在Sonogashira偶联反应中，由5-I-尿苷和合适的硼酸获得含有炔基接头的类似物。这尿嘧啶 设计此处提出的荧光类似物以满足以下要求：在不参与碱基配对的位置进行最小的化学修饰，导致相对较长的吸收和发射波长以及高量子产率。 5-（（4-甲氧基-苯基）-反式乙烯基）-2'-脱氧尿苷，6b，被发现是有前途的荧光探针。探针6b的量子产率比天然发色团（Φ0.12）大3000倍，最大发射（478 nm）与之相比发生了红移170 nm。尿苷，斯托克斯位移为143 nm。另外，由于探针6b采用了B-DNA所偏爱的抗构象和S糖折叠，所以它成为一种有希望的
• 5-Phenyluridine trihydrate
  作者：Thomas Pesnot、David L. Hughes、Gerd K. Wagner

  DOI：10.1107/s0108270107064177

  日期：2008.2.15

  In the title compound, C15H16N2O6 center dot similar to 3H(2)O, the substituted uracil ring is oriented in the anti position relative to the ribose ring, and the phenyl and uracil rings are oriented in a noncoplanar fashion. The furanose ring adopts a conformation close to 3'-endo, in contrast to the furanose conformation seen in the crystal structure of the synthetic precursor 5-bromouridine, which is close to 2'-endo. The molecule is involved in an extensive hydrogen-bonding network with several water molecules, some of which are disordered.
• CN115611816
  申请人：——

  公开号：——

  公开（公告）日：——