5-(2-naphthyl)-2'-deoxyuridine | 1373213-46-7

• 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-(2-naphthyl)-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-naphthalen-2-ylpyrimidine-2,4-dione
• CAS: 1373213-46-7
• 化学式: C₁₉H₁₈N₂O₅
• 分子量: 354.362
• InChiKey: YGPBLEHMWOBTTN-GVDBMIGSSA-N

物化性质

• 熔点：
  205 °C
• 密度：
  1.445±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-naphthyl)-2'-deoxyuridine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以65%的产率得到5-(2-naphthyl)-5'-O-dimethoxytrityl-2'-deoxyuridine
  参考文献：
  名称：

  Wavelength shifting oligonucleotide probe for the detection of adenosine of a target DNA with enhanced fluorescence signal

  摘要：

  The modulated photophysical property of strong electronically coupled naphthyl uridine linked via a single C-C bond was explored in DNA detection via wavelength shifting and enhanced fluorescence emission by a simple 'Just-Mix & Read' strategy of homogeneous DNA detection. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.031
• 作为产物：
  描述：

  Naphthalen-2-yl-di(propan-2-yloxy)borane 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 5-(2-naphthyl)-2'-deoxyuridine
  参考文献：
  名称：

  Wavelength shifting oligonucleotide probe for the detection of adenosine of a target DNA with enhanced fluorescence signal

  摘要：

  The modulated photophysical property of strong electronically coupled naphthyl uridine linked via a single C-C bond was explored in DNA detection via wavelength shifting and enhanced fluorescence emission by a simple 'Just-Mix & Read' strategy of homogeneous DNA detection. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.031

文献信息

• New water soluble Pd-imidate complexes as highly efficient catalysts for the synthesis of C5-arylated pyrimidine nucleosides
  作者：Anant Kapdi、Vijay Gayakhe、Yogesh S. Sanghvi、Joaquín García、Pedro Lozano、Ivan da Silva、José Pérez、J. Luis Serrano

  DOI：10.1039/c4ra01326c

  日期：——

  Recyclable water-soluble Pd complexes were revealed as excellent catalysts for Suzuki–Miyaura cross-coupling of challenging substrates like the antiviral nucleoside analogue 5-iodo-20-deoxyuridine.

  可回收水溶性Pd配合物被证明是Suzuki-Miyaura交叉偶联反应中优秀的催化剂，可用于具有挑战性底物的反应，例如抗病毒核苷类似物5-碘-20-脱氧尿嘧啶。
• Quadrol-Pd(<scp>ii</scp>) complexes: phosphine-free precatalysts for the room-temperature Suzuki–Miyaura synthesis of nucleoside analogues in aqueous media
  作者：José Luis Serrano、Sujeet Gaware、Jose Antonio Pérez、José Pérez、Pedro Lozano、Santosh Kori、Rambabu Dandela、Yogesh S. Sanghvi、Anant R. Kapdi

  DOI：10.1039/d1dt03778a

  日期：——

  Commercially available Quadrol, N,N,N′,N′-tetrakis(2-hydroxypropyl)ethylenediamine (THPEN), has been used for the first time as a N^N-donor neutral hydrophilic ligand in the synthesis and characterization of new water soluble palladium(II) complexes containing chloride, phthalimidate or saccharinate as co-ligands. [PdCl2(THPEN)] (1) [Pd(phthal)2(THPEN)] (2), [Pd(sacc)2(THPEN)] (3) and the analogous complex

  市售Quadrol， N , N , N ', N '-四(2-羟丙基)乙二胺(THPEN)，首次被用作N^N-供体中性亲水配体用于新水的合成和表征含有氯化物、邻苯二甲酰亚胺酸盐或糖精酸盐作为共配体的可溶性钯( II )络合物。 [PdCl 2 (THPEN)] ( 1 ) [Pd(酞) 2 (THPEN)] ( 2 ), [Pd(sacc) 2 (THPEN)] ( 3 ) 以及与密切相关的N , N , N的类似配合物', N '-四(2-羟乙基)乙二胺 (THEEN) [Pd(sacc) 2 (THEEN)] ( 4 ) 通过一锅反应由 [PdCl 2 (CH 3 CN) 2 ] 或 Pd 有效制备(OAc) 2 。通过单晶 X 射线衍射对1和3进行结构表征，产生了迄今为止报道的第一个钯与 Quadrol 配合物的结构。所得的钯配合物在水中高度溶解，并且被发现可作为无膦催化剂，在室温
• 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
• Extended fluorescent uridine analogues: synthesis, photophysical properties and selective interaction with BSA protein
  作者：Ajaykumar V. Ardhapure、Vijay Gayakhe、Shatrughn Bhilare、Anant R. Kapdi、Subhendu Sekhar Bag、Yogesh S. Sanghvi、Krishna Chaitanya Gunturu

  DOI：10.1039/d0nj02803g

  日期：——

  fluorescent nucleosides. The synthesis of these extended nucleoside analogues was carried out using Suzuki–Miyaura and Heck alkenylation reactions. A comparison of their photophysical properties allowed the identification of nucleosides 1g and 1h that exhibit the highest quantum yields in an aqueous solution. Studies on the binding interaction of the most promising fluorescent analogues, 1g and 1h, with serum

  2'-脱氧尿苷的荧光性质的改善是通过在尿苷的C–5位直接或通过烯基/苯基/苯乙烯基连接基引入（杂）芳族基团来创建生物学上有用的荧光核苷文库而实现的。这些扩展的核苷类似物的合成是使用Suzuki-Miyaura和Heck烯基化反应进行的。通过比较它们的光物理性质，可以鉴定出在水溶液中具有最高量子产率的核苷1g和1h。最有前途的荧光类似物1g和1h的结合相互作用的研究，与血清白蛋白蛋白相比，对α-淀粉酶对BSA蛋白具有极好的选择性。还进行了对接研究以预测核苷与BSA的特异性结合位点。