2-(2-hydroxyethylamino)-N-(4-phenoxyphenyl)acetamide | 230309-54-3

• 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-(2-hydroxyethylamino)-N-(4-phenoxyphenyl)acetamide
• CAS: 230309-54-3
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: GBUCKXUWSPWHJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethylamino)-N-(4-phenoxyphenyl)acetamide 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 Diisopropyl-phosphoramidous acid 2-{{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-acetyl}-[(4-phenoxy-phenylcarbamoyl)-methyl]-amino}-ethyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  DNA Conjugated Phenoxyaniline Intercalators: Synthesis of Diethanolaminoacetamide-type Linkers.

  摘要：

  Two non-nucleosidic monomers conjugated to a phenoxyaniline intercalator have been synthesized and inserted into ODNs. The conjugated monomers were prepared from 2-chloro-N-(4-phenoxyphenyl) acetamide (1) either by reaction with diethanolamine and 4,4'-dimethoxytritylation, or by reaction with ethanolamine by subsequent peptide coupling type reaction with 4,4'-dimethoxytrityl protected glycolic acid. The modified ODNs moderately stabilize DNA three-way junctions when the intercalator was introduced at the branch point. For targeting RNA the results were more ambiguous.

  DOI：

  10.3891/acta.chem.scand.53-0425
• 作为产物：
  描述：

  2-氯-N-(4-苯氧基苯基)乙酰胺 、 C.I.酸性橙108 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以81%的产率得到2-(2-hydroxyethylamino)-N-(4-phenoxyphenyl)acetamide
  参考文献：
  名称：

  DNA Conjugated Phenoxyaniline Intercalators: Synthesis of Diethanolaminoacetamide-type Linkers.

  摘要：

  Two non-nucleosidic monomers conjugated to a phenoxyaniline intercalator have been synthesized and inserted into ODNs. The conjugated monomers were prepared from 2-chloro-N-(4-phenoxyphenyl) acetamide (1) either by reaction with diethanolamine and 4,4'-dimethoxytritylation, or by reaction with ethanolamine by subsequent peptide coupling type reaction with 4,4'-dimethoxytrityl protected glycolic acid. The modified ODNs moderately stabilize DNA three-way junctions when the intercalator was introduced at the branch point. For targeting RNA the results were more ambiguous.

  DOI：

  10.3891/acta.chem.scand.53-0425

文献信息

• DNA Conjugated Phenoxyaniline Intercalators: Synthesis of Diethanolaminoacetamide-type Linkers.
  作者：Carina Storm Poulsen、Erik B. Pedersen、Claus Nielsen、Mia Helkearo、Harri Lönnberg、Shi-Ping Yan、Geng-Lin Wang、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0425

  日期：——

  Two non-nucleosidic monomers conjugated to a phenoxyaniline intercalator have been synthesized and inserted into ODNs. The conjugated monomers were prepared from 2-chloro-N-(4-phenoxyphenyl) acetamide (1) either by reaction with diethanolamine and 4,4'-dimethoxytritylation, or by reaction with ethanolamine by subsequent peptide coupling type reaction with 4,4'-dimethoxytrityl protected glycolic acid. The modified ODNs moderately stabilize DNA three-way junctions when the intercalator was introduced at the branch point. For targeting RNA the results were more ambiguous.