2-{3-[(3-{4-[3-({3-[(2-hydroxyethoxy)methyl]phenyl}ethynyl)phenyl]buta-1,3-diynyl}phenyl)ethynyl]benzyloxy}ethanol | 1162675-11-7

• 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: 2-{3-[(3-{4-[3-({3-[(2-hydroxyethoxy)methyl]phenyl}ethynyl)phenyl]buta-1,3-diynyl}phenyl)ethynyl]benzyloxy}ethanol
• 英文别名: 2-[[3-[2-[3-[4-[3-[2-[3-(2-Hydroxyethoxymethyl)phenyl]ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]phenyl]methoxy]ethanol；2-[[3-[2-[3-[4-[3-[2-[3-(2-hydroxyethoxymethyl)phenyl]ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]phenyl]methoxy]ethanol
• CAS: 1162675-11-7
• 化学式: C₃₈H₃₀O₄
• 分子量: 550.654
• InChiKey: HVGUAGUWKFRNQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{3-[(3-{4-[3-({3-[(2-hydroxyethoxy)methyl]phenyl}ethynyl)phenyl]buta-1,3-diynyl}phenyl)ethynyl]benzyloxy}ethanol 、 4,4'-双甲氧基三苯甲基氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到2-[3-({3-[4-(3-{[3-({2-[bis(4-methoxyphenyl)phenylmethoxy]ethoxy}methyl)phenyl]ethynyl}phenyl)buta-1,3-diynyl]phenyl}ethynyl)benzyloxy]ethanol
  参考文献：
  名称：

  三联体DNA中的第一个合成后5'-5'嵌入剂-固相合成后Sonogashira反应和芳基乙炔上的均偶联

  摘要：

  Abstractmagnified imageWe report herein a new technique for postsynthetic modifications of on‐column oligonucleotides. CPG‐Supported nonamer polypyrimidine oligodeoxynucleotides comprising 2‐(3‐iodobenzyloxy)ethyl phosphate at the terminal 5′‐ends were successfully capped with 1,3‐diethynylbenzene under Sonogashira reaction conditions, resulting in novel intercalating 5′‐5′ linker in alternate strand Hoogsteen triplex‐forming oligonucleotidej (TFO) X. In addition, novel 5′‐5′‐linked alternate strand TFOs, Y and Z, were isolated as a result of on‐column Sonogashira coupling with 1,3‐diethynylbenzene, followed by Cu‐catalyzed oxidative arylacetylenic homocoupling(s) between neighboring terminal arylacetylenes. Linkers X, Y, and Z represent the first postsynthesis 5′‐5′ intercalating linkers for alternate strand TFOs. Reproducibility and verification by independent syntheses using conventional phosphoramidite chemistry and DNA synthesis, as well as thermal stability and molecular modelling studies are included.

  DOI：

  10.1002/hlca.200800397
• 作为产物：
  描述：

  2-((3-iodobenzyl)oxy)ethanol 、 1,4-bis(3-ethynylphenyl)buta-1,3-diyne 在 copper(l) iodide 、 C₃₈H₃₂Cl₂P₂Pd 作用下， 以 三乙胺 为溶剂， 反应 17.0h， 以86%的产率得到2-{3-[(3-{4-[3-({3-[(2-hydroxyethoxy)methyl]phenyl}ethynyl)phenyl]buta-1,3-diynyl}phenyl)ethynyl]benzyloxy}ethanol
  参考文献：
  名称：

  三联体DNA中的第一个合成后5'-5'嵌入剂-固相合成后Sonogashira反应和芳基乙炔上的均偶联

  摘要：

  Abstractmagnified imageWe report herein a new technique for postsynthetic modifications of on‐column oligonucleotides. CPG‐Supported nonamer polypyrimidine oligodeoxynucleotides comprising 2‐(3‐iodobenzyloxy)ethyl phosphate at the terminal 5′‐ends were successfully capped with 1,3‐diethynylbenzene under Sonogashira reaction conditions, resulting in novel intercalating 5′‐5′ linker in alternate strand Hoogsteen triplex‐forming oligonucleotidej (TFO) X. In addition, novel 5′‐5′‐linked alternate strand TFOs, Y and Z, were isolated as a result of on‐column Sonogashira coupling with 1,3‐diethynylbenzene, followed by Cu‐catalyzed oxidative arylacetylenic homocoupling(s) between neighboring terminal arylacetylenes. Linkers X, Y, and Z represent the first postsynthesis 5′‐5′ intercalating linkers for alternate strand TFOs. Reproducibility and verification by independent syntheses using conventional phosphoramidite chemistry and DNA synthesis, as well as thermal stability and molecular modelling studies are included.

  DOI：

  10.1002/hlca.200800397

文献信息

• The First Postsynthetic 5′-5′ Intercalators in Triplex DNA - Solid-Phase Postsynthetic<i>Sonogashira</i>Reaction and Homocouplings on Arylacetylenes
  作者：Niels Bomholt、Vyacheslav V. Filichev、Erik B. Pedersen

  DOI：10.1002/hlca.200800397

  日期：2009.4

  Abstractmagnified imageWe report herein a new technique for postsynthetic modifications of on‐column oligonucleotides. CPG‐Supported nonamer polypyrimidine oligodeoxynucleotides comprising 2‐(3‐iodobenzyloxy)ethyl phosphate at the terminal 5′‐ends were successfully capped with 1,3‐diethynylbenzene under Sonogashira reaction conditions, resulting in novel intercalating 5′‐5′ linker in alternate strand Hoogsteen triplex‐forming oligonucleotidej (TFO) X. In addition, novel 5′‐5′‐linked alternate strand TFOs, Y and Z, were isolated as a result of on‐column Sonogashira coupling with 1,3‐diethynylbenzene, followed by Cu‐catalyzed oxidative arylacetylenic homocoupling(s) between neighboring terminal arylacetylenes. Linkers X, Y, and Z represent the first postsynthesis 5′‐5′ intercalating linkers for alternate strand TFOs. Reproducibility and verification by independent syntheses using conventional phosphoramidite chemistry and DNA synthesis, as well as thermal stability and molecular modelling studies are included.