1-benzoyloxy-2-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-6-(1,3-dioxan-2-yl)-4-iodobenzene | 685870-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-benzoyloxy-2-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-6-(1,3-dioxan-2-yl)-4-iodobenzene
• 英文别名: 1-benzoyloxy-2-(N-(3-dimethoxytrityloxyprop-1-yl)-aminocarbonyl)-6-(1,3-dioxan-2-yl)-4-iodobenzene；[2-[3-[Bis(4-methoxyphenyl)-phenylmethoxy]propylcarbamoyl]-6-(1,3-dioxan-2-yl)-4-iodophenyl] benzoate
• CAS: 685870-30-8
• 化学式: C₄₂H₄₀INO₈
• 分子量: 813.686
• InChiKey: NLBPGWGEJRRXMO-UHFFFAOYSA-N

物化性质

• 熔点：
  78-90 °C
• 沸点：
  852.2±65.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-二乙炔基苯 、 1-benzoyloxy-2-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-6-(1,3-dioxan-2-yl)-4-iodobenzene 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以64%的产率得到1,4-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]benzene
  参考文献：
  名称：

  Synthesis of Linear and Tripoidal Oligo(phenylene ethynylene)-Based Building Blocks for Application in Modular DNA-Programmed Assembly

  摘要：

  Rigid linear and tripoidal organic modules based on the oligo(phenylene ethynylene) backbone having salicylaldehyde-derived termini are synthesized. A highly functionalized 5-iodosalicyl aldehyde was prepared and coupled to each ethynyl group of 1,4-diethynylbenzene or 1,3,5-triethynylbenzene in Sonogashira couplings. The two or three termini of the compounds are functionalized for incorporation in linear and branched oligonucleotide strands. For the linear module (LM), the two termini are equipped with amide spacers, and one of these was functionalized with a DMTr (dimethoxytrityl)-protected hydroxy group and the other with a phosphoramidite. One of the tripoidal modules is prepared with DMTr groups in two of its three termini. A tripoidal module is also synthesized with three different groups on its hydroxy termini: a phosphoramidite, a DMTr group, and an Fmoc group. Extended studies have shown that these rigid linear and tripoidal organic modules can be incorporated into short oligonucleotides. Several of these modules can be applied for DNA-directed assembly and covalent coupling into structures of predetermined connectivity. Such structures have potential application for molecular electronics and nanotechnology.

  DOI：

  10.1021/jo035764m
• 作为产物：
  描述：

  5-碘水杨酸 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 1-benzoyloxy-2-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-6-(1,3-dioxan-2-yl)-4-iodobenzene
  参考文献：
  名称：

  Synthesis of Linear and Tripoidal Oligo(phenylene ethynylene)-Based Building Blocks for Application in Modular DNA-Programmed Assembly

  摘要：

  Rigid linear and tripoidal organic modules based on the oligo(phenylene ethynylene) backbone having salicylaldehyde-derived termini are synthesized. A highly functionalized 5-iodosalicyl aldehyde was prepared and coupled to each ethynyl group of 1,4-diethynylbenzene or 1,3,5-triethynylbenzene in Sonogashira couplings. The two or three termini of the compounds are functionalized for incorporation in linear and branched oligonucleotide strands. For the linear module (LM), the two termini are equipped with amide spacers, and one of these was functionalized with a DMTr (dimethoxytrityl)-protected hydroxy group and the other with a phosphoramidite. One of the tripoidal modules is prepared with DMTr groups in two of its three termini. A tripoidal module is also synthesized with three different groups on its hydroxy termini: a phosphoramidite, a DMTr group, and an Fmoc group. Extended studies have shown that these rigid linear and tripoidal organic modules can be incorporated into short oligonucleotides. Several of these modules can be applied for DNA-directed assembly and covalent coupling into structures of predetermined connectivity. Such structures have potential application for molecular electronics and nanotechnology.

  DOI：

  10.1021/jo035764m

文献信息

• Synthesis of an elongated linear oligo(phenylene ethynylene)-based building block for application in DNA-programmed assembly
  作者：Peter Blakskjær、Kurt V. Gothelf

  DOI：10.1039/b605844b

  日期：——

  The synthesis of an elongated linear oligonucleotide-functionalised module (ELOM) is described. The ELOM structure is based on an oligo(phenylene ethynylene) backbone substituted with two decyloxy groups. The two termini constitute two salicylaldehyde moieties acting as chemical cross-linkers. Before incorporation into an oligonucleotide sequence the organic part of the module, the elongated linear module (ELM), is functionalised with a dimethoxytrityl group and a phosphoramidite group. This enables incorporation into the middle of 30-mer oligonucleotide sequences by automated DNA synthesis. The obtained ELOMs were characterised by polyacrylamide gel electrophoresis and MALDI-TOF mass spectrometry. In analogy with previously reported LOM and TOM structures the coupling reactions of the ELOM modules were tested.

  描述了一种延长的线性寡核苷酸功能化模块（ELOM）的合成。ELOM结构基于一个取代有两个癸氧基团的寡（苯乙炔）骨架。其两个末端由作为化学交联剂的两个水杨醛部分构成。在被纳入到寡核苷酸序列之前，该模块的有机部分，即延长的线性模块（ELM），被功能化为含有二甲氧基三苯甲基基团和磷酰胺基团的形式。这使得它能够通过自动化的DNA合成过程被插入到30碱基长的寡核苷酸序列的中间。获得的ELOMs通过聚丙烯酰胺凝胶电泳和MALDI-TOF质谱分析进行了表征。参照先前报道的LOM和TOM结构，测试了ELOM模块的偶联反应。