5-(pyrene-1-yl)-2'-deoxyuridine | 167105-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5-(pyrene-1-yl)-2'-deoxyuridine
• 英文别名: 5-(pyren-1-yl)-2'-deoxyuridine；5-(1-pyrenyl)-2'-deoxyuridine；5-pyrenyl-2'-deoxyuridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-pyren-1-ylpyrimidine-2,4-dione
• CAS: 167105-67-1
• 化学式: C₂₅H₂₀N₂O₅
• 分子量: 428.444
• InChiKey: YICBKTASDXKCQP-PWRODBHTSA-N

物化性质

• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  碘苷 在 四(三苯基膦)钯 吡啶 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 58.0h， 生成 5-(pyrene-1-yl)-2'-deoxyuridine
  参考文献：
  名称：

  通过 Suzuki-Miyaura 交叉偶联反应制备芘基修饰的核苷

  摘要：

  通过钯催化的芘-1-基硼酸 (3) 的 Suzuki-Miyaura 交叉偶联反应合成了修饰的核苷 5-芘基-2'-脱氧尿苷 (1) 和 8-芘基-2'-脱氧鸟苷 (2)分别连接到 5-iodo-2'-deoxyuridine (4) 或 8-bromo-2'-deoxyguanosine (7)。在制备过程中不需要用于核苷的羟基和氨基官能团的保护基团。两种芘衍生物都是适用于还原电子转移（1）或氧化空穴转移（2）光谱研究的核苷模型。

  DOI：

  10.1055/s-2002-25349

文献信息

• Water-Soluble Pd–Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling
  作者：Vijay Gayakhe、Ajaykumar Ardhapure、Anant R. Kapdi、Yogesh S. Sanghvi、Jose Luis Serrano、Luis García、Jose Pérez、Joaquím García、Gregorio Sánchez、Christian Fischer、Carola Schulzke

  DOI：10.1021/acs.joc.5b02475

  日期：2016.4.1

  A broadly applicable catalyst system consisting of water-soluble Pd–imidate complexes has been enployed for the Suzuki–Miyaura cross-coupling of four different nucleosides in water under mild conditions. The efficient nature of the catalyst system also allowed its application in developing a microwave-assisted protocol with the purpose of expediting the catalytic reaction. Preliminary mechanistic studies

  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。
• A Model Nucleoside for Electron Injection into DNA: 5-Pyrenyl-2′-Deoxyribose This work was supported by the Deutsche Forschungsgemeinschaft (Wa 1386/7-1, Fi 721/3-1,3-4) and by the Fonds der Chemischen Industrie. N.A. and H.A.W. are grateful to Professor Horst Kessler, Technische Universität München, for the generous support.
  作者：Nicole Amann、Evgeni Pandurski、Torsten Fiebig、Hans-Achim Wagenknecht

  DOI：10.1002/1521-3773(20020816)41:16<2978::aid-anie2978>3.0.co;2-5

  日期：2002.8.16
• Photophysics of 2'-Deoxyuridine (dU) Nucleosides Covalently Substituted with Either 1-Pyrenyl or 1-Pyrenoyl: Observation of Pyrene-to-Nucleoside Charge-Transfer Emission in 5-(1-Pyrenyl)-dU
  作者：Thomas L. Netzel、Min Zhao、Kambiz Nafisi、Jeb Headrick、Matthew S. Sigman、Bruce E. Eaton

  DOI：10.1021/ja00141a002

  日期：1995.9

  This paper reports syntheses, electronic absorbance and emission spectra, and emission kinetics results for two types of pyrene-substituted uridine nucleosides as part of an ongoing study which is examining the photophysical and photochemical behaviors of these same nucleosides embedded in DNA oligomers and duplexes with varying base-sequence composition, The two labels are 1-pyrenyl itself and 1-carboxypyrenyl (1-pyrenoyl) which are each joined directly to the 5-position of 2'-deoxyuridine (dU), These direct attachments significantly restrict the range of conformations available to the pyrene label when it is attached to a DNA oligomer or duplex. pi,pi* emission is absent for 5-(1-pyrenyl)-dU, 1, in methanol (MeOH) but present in tetrahydrofuran (THF). For 1 in MeOH, broad charge-transfer (CT) emission is present with a maximum at 470 nm and a quantum yield of 0.027; for 1 in THF, pi,pi* emission is present with a maximum at 395 nm and quantum yield of 0.42. Thermodynamic considerations suggest that the CT photoproduct of 1 which emits in MeOK is pyrene(.+)/dU(.-). The emission kinetics of 1 in MeOH are triexponential, but the wavelength variation of the relative amplitudes of the different decay lifetimes indicates that the CT-state relaxations are biexponential with lifetimes of less than or equal to 50 ps and 0.9 ns, Similarly, the pi,pi* State of 1 in MeOH also has two electron transfer (ET) quenching lifetimes of less than or equal to 50 ps and 2-3 ns. The steady-state emission spectrum of 1 in MeOH shows that emission from the few long-lived pi,pi*: states is dominated at all wavelengths by the 0.9-ns lived CT emission, In contrast, only pi,pi* emission is observed for 5-(1-pyrenoyl)-dU, 2, in both MeOH and THF with emission quantum yields of 0.002 and 0.028, respectively. The emission kinetics for 2 in THF are at least quadruply exponential having the longest emission lifetime of ca. 95 ns. However, only about 10% of the relative emission amplitude decays with lifetimes greater than 10 ns. Approximately 90% of the emission amplitude decays on the same time scale as for 2 in MeOH, The spectral and emission kinetics data for nucleosides 1 and 2 support the conclusions that each has multiple conformers in solution and that the relative orientation of the pyrene and uridine pi-systems plays a crucial role in determining the rates of both ET quenching of pyrene* and charge-recombination in the photoproduct.
• Preparation of Pyrenyl-Modified Nucleosides via Suzuki-Miyaura Cross-Coupling Reactions
  作者：Nicole Amann、Hans-Achim Wagenknecht

  DOI：10.1055/s-2002-25349

  日期：——

  The modified nucleosides 5-pyrenyl-2'-deoxyuridine (1) and 8-pyrenyl-2'-deoxyguanosine (2) were synthesized via palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of pyren-1-yl boronic acid (3) to either 5-iodo-2'-deoxyuridine (4), or 8-bromo-2'-deoxyguanosine (7), respectively. No protecting groups for the hydroxy and amino functions of the nucleoside are needed during the preparation. Both

  通过钯催化的芘-1-基硼酸 (3) 的 Suzuki-Miyaura 交叉偶联反应合成了修饰的核苷 5-芘基-2'-脱氧尿苷 (1) 和 8-芘基-2'-脱氧鸟苷 (2)分别连接到 5-iodo-2'-deoxyuridine (4) 或 8-bromo-2'-deoxyguanosine (7)。在制备过程中不需要用于核苷的羟基和氨基官能团的保护基团。两种芘衍生物都是适用于还原电子转移（1）或氧化空穴转移（2）光谱研究的核苷模型。