N,N'-bis(2-hydroxyethyl)-2,2'-oxidiacetamide | 66671-69-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(2-hydroxyethyl)-2,2'-oxidiacetamide
• 英文别名: N,N'-bis(2-hydroxyethyl)-2,2'-oxydiacetamide；oxydi-acetic acid bis-(2-hydroxy-ethylamide)；Oxydi-essigsaeure-bis-(2-hydroxy-aethylamid)；Diglykolsaeure-bis-(2-hydroxy-aethylamid)；N-(2-hydroxyethyl)-2-[2-(2-hydroxyethylamino)-2-oxoethoxy]acetamide
• CAS: 66671-69-0
• 化学式: C₈H₁₆N₂O₅
• 分子量: 220.225
• InChiKey: AADFNTBAEGWBCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-hydroxyethyl)-2,2'-oxidiacetamide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[3-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)ethyl]-N'-[2-(4,4'-dimethoxytrityl)oxyethyl]-2,2'-oxidiacetamide
  参考文献：
  名称：

  Synthesis and Evaluation of New Spacers for Use as dsDNA End-Caps

  摘要：

  A series of aliphatic and aromatic spacer molecules designed to cap the ends of DNA duplexes have been synthesized. The spacers were converted into dimethoxytrityl-protected phosphoramidites as synthons for oligonucleotides synthesis. The effect of the spacers on the stability of short DNA duplexes was assessed by melting temperature studies. End-caps containing amide groups were found to be less stabilizing than the hexaethylene glycol spacer. End-caps containing either a terthiophene or a naphthalene tetracarboxylic acid diimidc were found to be significantly more stabilizing. The former showed a preference for stacking above an A.T base pair. Spacers containing only methylene (-CH2-) and amide (-CONH-) groups interact weakly with DNA and consequently may be optimal for applications that require minimal influence on DNA structure but require a way to hold the ends of double-stranded DNA together.

  DOI：

  10.1021/bc100202y
• 作为产物：
  描述：

  N,N'-bis[2-(tert-butyldimethylsilyloxy)ethyl]-2,2'-oxidiacetamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以94%的产率得到N,N'-bis(2-hydroxyethyl)-2,2'-oxidiacetamide
  参考文献：
  名称：

  Synthesis and Evaluation of New Spacers for Use as dsDNA End-Caps

  摘要：

  A series of aliphatic and aromatic spacer molecules designed to cap the ends of DNA duplexes have been synthesized. The spacers were converted into dimethoxytrityl-protected phosphoramidites as synthons for oligonucleotides synthesis. The effect of the spacers on the stability of short DNA duplexes was assessed by melting temperature studies. End-caps containing amide groups were found to be less stabilizing than the hexaethylene glycol spacer. End-caps containing either a terthiophene or a naphthalene tetracarboxylic acid diimidc were found to be significantly more stabilizing. The former showed a preference for stacking above an A.T base pair. Spacers containing only methylene (-CH2-) and amide (-CONH-) groups interact weakly with DNA and consequently may be optimal for applications that require minimal influence on DNA structure but require a way to hold the ends of double-stranded DNA together.

  DOI：

  10.1021/bc100202y

文献信息

• Nu-substituted amide and method for preparing the same
  申请人：DU PONT

  公开号：US02347494A1

  公开（公告）日：1944-04-25
• Synthesis and Evaluation of New Spacers for Use as dsDNA End-Caps
  作者：Pei-Sze Ng、Brian M. Laing、Ganesan Balasundarum、Maneesh Pingle、Alan Friedman、Donald E. Bergstrom

  DOI：10.1021/bc100202y

  日期：2010.8.18

  A series of aliphatic and aromatic spacer molecules designed to cap the ends of DNA duplexes have been synthesized. The spacers were converted into dimethoxytrityl-protected phosphoramidites as synthons for oligonucleotides synthesis. The effect of the spacers on the stability of short DNA duplexes was assessed by melting temperature studies. End-caps containing amide groups were found to be less stabilizing than the hexaethylene glycol spacer. End-caps containing either a terthiophene or a naphthalene tetracarboxylic acid diimidc were found to be significantly more stabilizing. The former showed a preference for stacking above an A.T base pair. Spacers containing only methylene (-CH2-) and amide (-CONH-) groups interact weakly with DNA and consequently may be optimal for applications that require minimal influence on DNA structure but require a way to hold the ends of double-stranded DNA together.