methyl 4-[(E)-2-(pentafluorophenyl)vinyl]benzoate

• 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-(pentafluorophenyl)vinyl]benzoate
• 英文别名: (E)-methyl 4-(perfluorostyryl)benzoate；methyl 4-[(E)-2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzoate
• 化学式: C₁₆H₉F₅O₂
• 分子量: 328.238
• InChiKey: CFUNSTARSKATNS-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,3,4,5,6-五氟苯乙烯	2,3,4,5,6-pentafluorostyrene	653-34-9	C8H3F5	194.104

反应信息

• 作为反应物：
  描述：

  methyl 4-[(E)-2-(pentafluorophenyl)vinyl]benzoate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到4-[(E)-2-(pentafluorophenyl)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：

  五氟苯甲醛 、 (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73%的产率得到methyl 4-[(E)-2-(pentafluorophenyl)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

• Synthesis of Tailored Perfluoro Unsaturated Monomers for Potential Applications in Proton Exchange Membrane Preparation
  作者：Antonio Monopoli、Michele Casiello、Pietro Cotugno、Antonella Milella、Fabio Palumbo、Francesco Fracassi、Angelo Nacci

  DOI：10.3390/molecules26185592

  日期：——

  proton transport capacity of the resulting membrane, (iii) both aliphatic and aromatic perfluorinated tags to diversify the membrane polarity with respect to Nafion®, and (iv) a double bond to facilitate the polymerization under vacuum giving a preferential way for the chain growth of the polymer. A retrosynthetic approach persuaded us to attempt three main synthetic strategies: (a) organometallic Heck-type

  目前工作的目的是合成和表征新的全氟化单体，类似于 Nafion ®，用于质子传输的酸性基团，用于质子交换膜 (PEM) 燃料电池的潜在和未来应用。为此，我们将注意力集中在各种分子的合成上，这些分子具有 (i) 足够的挥发性，可用于真空聚合技术（例如 PECVD）），（ii）磺酸、膦酸或羧酸官能团的质子传输能力所得膜，(iii) 脂肪族和芳香族全氟化标签，使膜极性相对于 Nafion ®多样化, 和 (iv) 双键以促进真空下的聚合，为聚合物的链增长提供优先方式。逆合成方法说服我们尝试三种主要的合成策略：（a）有机金属 Heck 型交叉偶联，（b）亲核置换，和（c）Wittig-Horner 反应（碳负离子方法）。还介绍了聚合物薄膜等离子沉积的初步结果。等离子体条件的变化使我们能够指出，在最温和的设置 (20 W) 下制备的薄膜在其结构中显示出最大的单体保留。在这种情况下，等离子体聚合可能主要通过单体分子中的
• 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.