methyl 4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]benzoate | 360789-58-8

• 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: methyl 4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]benzoate
• 英文别名: 4-<2-(3,4,5-trimethoxyphenyl)ethenyl>benzoic acid methyl ester；methyl 4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzoate
• CAS: 360789-58-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: KXTRNIBEDPYVKX-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]benzoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到(E)-4-[2-(3,4,5-trimethoxyphenyl)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
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 (4-甲氧羰基苄基)三苯基溴化膦 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.08h， 以53%的产率得到methyl 4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]benzoate
  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

文献信息

• Metalated Aromatic Carboxylic Acids: Improved Synthesis of SDZ HUL412
  作者：John C. Amedio、Ustun B. Sunay、Oljan Repic

  DOI：10.1080/00397919508011404

  日期：1995.3

  Abstract Synthesis of aryl methyl ester 2 is described utilizing a metalation-condensation and a metalation-alkylation sequence starting from the dianion of p-toluic acid generated in an aprotic solvent medium.

  摘要 描述了使用金属化-缩合和金属化-烷基化序列合成芳基甲酯 2，该序列从在非质子溶剂介质中产生的对甲苯甲酸的二价阴离子开始。
• 5‘-Tethered Stilbene Derivatives as Fidelity- and Affinity-Enhancing Modulators of DNA Duplex Stability
  作者：Zeynep Dogan、Ralph Paulini、Jan A. Rojas Stütz、Sukunath Narayanan、Clemens Richert

  DOI：10.1021/ja0394434

  日期：2004.4.1

  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.