1,3-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]-5-[[4-benzoyloxy-5-[[(3-hydroxyprop-1-yl)amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]benzene | 685870-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 1,3-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]-5-[[4-benzoyloxy-5-[[(3-hydroxyprop-1-yl)amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]benzene
• CAS: 685870-38-6
• 化学式: C₁₁₇H₁₀₅N₃O₂₂
• 分子量: 1905.13
• InChiKey: GZFZLNQQCHSYMF-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 1,3-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]-5-[[4-benzoyloxy-5-[[(3-hydroxyprop-1-yl)amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]benzene 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以74%的产率得到1,3-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]-5-[[4-benzoyloxy-5-[[[3-[[[(9-fluorenyl)methoxy]carbonyl]oxy]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：

  1,3,5-tris[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]benzene 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 以28%的产率得到1,3-bis[[4-benzoyloxy-5-[[[3-(4,4'-dimethoxytrityloxy)prop-1-yl]amino]carbonyl]-3-(1,3-dioxan-2-yl)phenyl]ethynyl]-5-[[4-benzoyloxy-5-[[(3-hydroxyprop-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