5-[3-(6-dimethylamino-2-naphthyl)-3-oxo-2-propynyl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyuridine | 939026-13-8

• 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-[3-(6-dimethylamino-2-naphthyl)-3-oxo-2-propynyl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-[3-[6-(dimethylamino)naphthalen-2-yl]-3-oxoprop-1-ynyl]pyrimidine-2,4-dione
• CAS: 939026-13-8
• 化学式: C₃₆H₅₁N₃O₆Si₂
• 分子量: 677.988
• InChiKey: ABKDXBVAIKGLEM-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[3-(6-dimethylamino-2-naphthyl)-3-oxo-2-propynyl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyuridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以68%的产率得到5-[3-(6-dimethylamino-2-naphthyl)-3-oxo-2-propynyl]-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and fluorescence properties of dimethylaminonaphthalene–deoxyuridine conjugates as polarity-sensitive probes

  摘要：

  The design of probes for monitoring various structures and dynamics of DNA and its surroundings is an important step in understanding biological events accompanying interbiomolecular interaction. We have developed novel fluorescent nucleosides in which the uracil base and the fluorophore are tethered by rigid linkers. They show unique absorption and fluorescence emission spectra. Nucleoside 2 is a fluorophore with high CT character and the fluorescence is very sensitive to solvent polarity. Nucleoside 3 shows absorption and emission maxima with longer wavelength due to extension of the DAN-conjugate system. These fluorophore-deoxyuridine conjugates with unique fluorescence properties would work as reporter probes sensitive to the change in microenvironment around specific sites of DNA. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.113
• 作为产物：
  描述：

  6-dimethylamino-2-(3-trimethylsilyl-1-hydroxy-2-propynyl)naphthalene 在 四(三苯基膦)钯 manganese(IV) oxide 、 copper(l) iodide 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 5-[3-(6-dimethylamino-2-naphthyl)-3-oxo-2-propynyl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and fluorescence properties of dimethylaminonaphthalene–deoxyuridine conjugates as polarity-sensitive probes

  摘要：

  The design of probes for monitoring various structures and dynamics of DNA and its surroundings is an important step in understanding biological events accompanying interbiomolecular interaction. We have developed novel fluorescent nucleosides in which the uracil base and the fluorophore are tethered by rigid linkers. They show unique absorption and fluorescence emission spectra. Nucleoside 2 is a fluorophore with high CT character and the fluorescence is very sensitive to solvent polarity. Nucleoside 3 shows absorption and emission maxima with longer wavelength due to extension of the DAN-conjugate system. These fluorophore-deoxyuridine conjugates with unique fluorescence properties would work as reporter probes sensitive to the change in microenvironment around specific sites of DNA. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.113