4-{(E)-2-[4-({[(allyloxy)carbonyl]amino}methyl)phenyl]vinyl}benzoic acid | 1007859-60-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-{(E)-2-[4-({[(allyloxy)carbonyl]amino}methyl)phenyl]vinyl}benzoic acid
• CAS: 1007859-60-0
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: DWGLSZWWAIQVOP-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-{(E)-2-[4-({[(allyloxy)carbonyl]amino}methyl)phenyl]vinyl}benzoic acid 在 二异丙基铵盐四氮唑 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.25h， 生成 3-[4-{(E)-2-[4-(allyloxycarbonyl)aminomethylphenyl]vinyl}benzocarbonyl]-3-(aminopropyl)-1-O-cyanoethyl-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  5‘-Tethered Stilbene Derivatives as Fidelity- and Affinity-Enhancing Modulators of DNA Duplex Stability

  摘要：

  A series of 5'-linked stilbene-DNA conjugates with different substituents in the distal aromatic ring of the stilbene was prepared, and the effect of the modifications on duplex stability was determined via UV-melting curves. A trimethoxystilbene derivative as a 5'-substituent increases duplex melting points by up to 12.2 degrees C per modification. With this alkoxystilbene substituent, terminal mismatches in DNA duplexes lower the melting point by up to 23.4 degrees C over the perfectly matched control, whereas terminal mismatches in unmodified DNA cause melting point depressions of no more than 6.1 degrees C. An aminomethylstilbene substituent linked to an oligopyrrolamide minor groove binder increases the melting point of an all-A/T decamer by up to 32.7 degrees C, thus shifting the melting point into a range typical for duplexes with statistical G/C-content. An affinity- and selectivity-enhancing effect was also observed when the trimethoxystilbene cap was employed on a small DNA microarray. The phosphoramidite of the trimethoxystilbene can be readily employed in automatic DNA synthesis, facilitating the generation of DNA chips with improved fidelity.

  DOI：

  10.1021/ja0394434
• 作为产物：
  描述：

  methyl 4-{(E)-2-[4-({[(allyloxy)carbonyl]amino}methyl)phenyl]vinyl}benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以91%的产率得到4-{(E)-2-[4-({[(allyloxy)carbonyl]amino}methyl)phenyl]vinyl}benzoic acid
  参考文献：
  名称：

  5‘-Tethered Stilbene Derivatives as Fidelity- and Affinity-Enhancing Modulators of DNA Duplex Stability

  摘要：

  A series of 5'-linked stilbene-DNA conjugates with different substituents in the distal aromatic ring of the stilbene was prepared, and the effect of the modifications on duplex stability was determined via UV-melting curves. A trimethoxystilbene derivative as a 5'-substituent increases duplex melting points by up to 12.2 degrees C per modification. With this alkoxystilbene substituent, terminal mismatches in DNA duplexes lower the melting point by up to 23.4 degrees C over the perfectly matched control, whereas terminal mismatches in unmodified DNA cause melting point depressions of no more than 6.1 degrees C. An aminomethylstilbene substituent linked to an oligopyrrolamide minor groove binder increases the melting point of an all-A/T decamer by up to 32.7 degrees C, thus shifting the melting point into a range typical for duplexes with statistical G/C-content. An affinity- and selectivity-enhancing effect was also observed when the trimethoxystilbene cap was employed on a small DNA microarray. The phosphoramidite of the trimethoxystilbene can be readily employed in automatic DNA synthesis, facilitating the generation of DNA chips with improved fidelity.

  DOI：

  10.1021/ja0394434