3-benzoyl-1-(4-iodophenyl)-5-methylpyrimidine-2,4(1H,3H)-dione | 917081-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzoyl-1-(4-iodophenyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 3-Benzoyl-1-(4-iodophenyl)-5-methylpyrimidine-2,4-dione
• CAS: 917081-96-0
• 化学式: C₁₈H₁₃IN₂O₃
• 分子量: 432.217
• InChiKey: TUNSZNPQGJTAJD-UHFFFAOYSA-N

物化性质

• 熔点：
  246-247 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  520.2±52.0 °C(Predicted)
• 密度：
  1.687±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-(4-iodophenyl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 copper(l) iodide 、 四(三苯基膦)钯 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 5'-O-dimethoxytrityl-5-(4-(thymin-1-yl)phenyl)ethynyl-2'-deoxyuridine
  参考文献：
  名称：

  Double-headed nucleotides introducing thymine nucleobases in the major groove of nucleic acid duplexes

  摘要：

  通过Sonogashira和Suzuki偶联合成了四个双头核苷酸，并引入到核酸双链中。

  DOI：

  10.1039/c5ob00872g
• 作为产物：
  描述：

  胸腺嘧啶 在 吡啶 、 copper diacetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 104.0h， 生成 3-benzoyl-1-(4-iodophenyl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of Rigid Rod, Trigonal, and Tetrahedral Nucleobase-Terminated Molecules

  摘要：

  一个高效的片段拼接方法已经被开发出来，用于构建多个以核酸碱基为终止的单体。在适中到良好的产率下生成了构象固定的棒状、三角平面和四面体的胸腺嘧啶和腺嘧啶结构，这将作为探索核酸碱基作为超分子化学中天然氢键组分的启发性例子。

  DOI：

  10.1055/a-1695-0820

文献信息

• Synthesis of Rigid Homo- and Heteroditopic Nucleobase-Terminated Molecules Incorporating Adenine and/or Thymine
  作者：Mikkel F. Jacobsen、Casper S. Andersen、Martin M. Knudsen、Kurt V. Gothelf

  DOI：10.1021/ol071006x

  日期：2007.7.1

  A series of homo- and heteroditopic thymine- and/or adenine-terminated molecules incorporating rigid aryl or oligo(phenylene ethynylene) linkers has been efficiently synthesized. The key steps involved in the synthesis are the construction of the N-arylated nucleobases using the Chan-Lam-Evans-modified Ullman coupling and their further elaboration using the Sonogashira coupling. Furthermore, the synthesis

  已经有效地合成了一系列掺有刚性芳基或低聚（亚苯基亚乙炔基）连接基的，在异位和异位胸腺嘧啶和/或腺嘌呤封端的分子。合成中涉及的关键步骤是使用Chan-Lam-Evans修饰的Ullman偶联物构建N-芳基化核苷碱基，并使用Sonogashira偶联物进行进一步加工。此外，据报道合成了刚性的三脚架胸腺嘧啶衍生物。
• Efficient <i>N</i>-Arylation and <i>N</i>-Alkenylation of the Five DNA/RNA Nucleobases
  作者：Mikkel F. Jacobsen、Martin M. Knudsen、Kurt V. Gothelf

  DOI：10.1021/jo061694i

  日期：2006.11.1

  [GRAPHICS]A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged readily in the copper-mediated Chan-Lam-Evans-modified Ullmann condensation with a range of different boronic acids at room temperature and were subsequently converted to the corresponding deprotected or unmasked adducts. Different N-3-protecting groups were examined in the case of thymine, where the benzoyl group afforded the highest yields. A 4-alkylthio-substituted pyrimidin-2(1H)-one served as both a cytosine and a uracil precursor and was N-arylated and N-alkenylated in high yields. Adenine was efficiently and selectively N-arylated and N-alkenylated at the N-9 position by employing a bis-Boc-protected adenine derivative, while a bis-Boc-protected 2-amino-6-chloropurine served as guanine precursor and could also be selectively N-9-arylated and N-9-alkenylated.