2-ethyl-6-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1574318-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-ethyl-6-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS: 1574318-72-1
• 化学式: C₂₅H₂₁N₃O₇
• 分子量: 475.458
• InChiKey: VUAGWDQUYYBACM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  141.93
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  6-bromo-2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)dione 在 dipotassium hydrogenphosphate 、 copper(l) iodide 、 四(三苯基膦)钯 、 2C₂H₃O₂^(1-)*2C₆H₇N₃O₂^(2-)*4Na⁽¹⁺⁾*Pd⁽²⁺⁾ 、 potassium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 2-ethyl-6-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Chemical Labeling of 5-Iodo-2′-deoxyuridine with 4-Ethynyl-N-ethyl-1,8-naphthalimide Using Copper-Free Sonogashira Cross-Coupling in Aqueous Medium

  摘要：

  The utility of Sonogashira cross-coupling reactions in organic synthesis is indisputable. However, the palladium catalytic Sonogashira reaction in mild condition is still in its infancy. Here, we reported the synthesis of a fluorescent nucleoside analog by using a copper-free Sonogashira cross-coupling reaction in a satisfactory yield. This reaction occurred at 37 degrees C in the open air and aqueous medium, and avoided the toxicity of Cu(I). The mild Sonogashira reaction provided the possibility of fluorescent labeling of nucleoside mimics in living cells. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.841937