N,N-bis[2-(4,4'-dimethoxytrityloxy)ethyl]amine | 516462-78-5

• 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: N,N-bis[2-(4,4'-dimethoxytrityloxy)ethyl]amine
• 英文别名: 2-[bis(4-methoxyphenyl)-phenylmethoxy]-N-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethyl]ethanamine
• CAS: 516462-78-5
• 化学式: C₄₆H₄₇NO₆
• 分子量: 709.882
• InChiKey: HNGCTDQVAXJBSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-bis[2-(4,4'-dimethoxytrityloxy)ethyl]amine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-[2-hydroxyethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’,N’-bis[2-(4,4’-dimethoxytrityloxy)ethyl]glutaramide
  参考文献：
  名称：

  Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion

  摘要：

  Non-nucleotide phosporamidites were synthetized, having a branching backbone with different positions for functional groups. Phosphoramidite monomers obtained contain intercalator moiety, 6-chloro-2-methoxyacridine, and additional hydroxyl residue protected with dimethoxytrityl group or with the tert-butyldimethylsilyl group for post-synthetic modification. Oligothymidilates containing one or more modified units in different positions of the sequence were synthesized. The melting point and thermodynamic parameters of the formation of complementary duplexes formed by modified oligonucleotides were defined (change in enthalpy and entropy). The introduction of intercalating residue causes a significant stabilization of DNA duplexes. It is shown that the efficiency of the fluorescence of acridine residue in the oligonucleotide conjugate significantly changes upon hybridization with DNA.

  DOI：

  10.1134/s106816201206009x
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 哌啶 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N,N-bis[2-(4,4'-dimethoxytrityloxy)ethyl]amine
  参考文献：
  名称：

  Synthesis of Triple Helix Forming Oligonucleotides with a Phenanthroline Moiety into the 3′-3′ Inversion Site of Polarity

  摘要：

  A protocol for the synthesis of triplex forming oligonucleotides containing a chelating molecule in the 3'-3' inversion site of polarity is reported. A number of 16-mers have been synthesized and UV spectroscopy employed to evaluate the stability of their triple helix complexes with the pertinent double-strand oligonucleotide targets. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:24<4228::aid-ejoc4228>3.0.co;2-n

文献信息

• Synthesis of Triple Helix Forming Oligonucleotides with a Phenanthroline Moiety into the 3′-3′ Inversion Site of Polarity
  作者：Veronica Esposito、Aldo Galeone、Luciano Mayol、Giorgia Oliviero、Antonio Randazzo、Michela Varra

  DOI：10.1002/1099-0690(200212)2002:24<4228::aid-ejoc4228>3.0.co;2-n

  日期：2002.12

  A protocol for the synthesis of triplex forming oligonucleotides containing a chelating molecule in the 3'-3' inversion site of polarity is reported. A number of 16-mers have been synthesized and UV spectroscopy employed to evaluate the stability of their triple helix complexes with the pertinent double-strand oligonucleotide targets. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).
• Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion
  作者：M. S. Kupryushkin、D. V. Pyshnyi

  DOI：10.1134/s106816201206009x

  日期：2012.11

  Non-nucleotide phosporamidites were synthetized, having a branching backbone with different positions for functional groups. Phosphoramidite monomers obtained contain intercalator moiety, 6-chloro-2-methoxyacridine, and additional hydroxyl residue protected with dimethoxytrityl group or with the tert-butyldimethylsilyl group for post-synthetic modification. Oligothymidilates containing one or more modified units in different positions of the sequence were synthesized. The melting point and thermodynamic parameters of the formation of complementary duplexes formed by modified oligonucleotides were defined (change in enthalpy and entropy). The introduction of intercalating residue causes a significant stabilization of DNA duplexes. It is shown that the efficiency of the fluorescence of acridine residue in the oligonucleotide conjugate significantly changes upon hybridization with DNA.