(E)-1-chloro-3-(4-fluorostyryl)benzene | 24959-64-6

• 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: (E)-1-chloro-3-(4-fluorostyryl)benzene
• 英文别名: trans-4-Fluor-3'-chlorstilben；1-chloro-3-[(E)-2-(4-fluorophenyl)vinyl]benzene；(E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene；1-chloro-3-[(E)-2-(4-fluorophenyl)ethenyl]benzene
• CAS: 24959-64-6
• 化学式: C₁₄H₁₀ClF
• 分子量: 232.685
• InChiKey: AJDZYQASTHHFTK-SNAWJCMRSA-N

物化性质

• 沸点：
  324.4±21.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-chloro-3-(4-fluorostyryl)benzene 在 对甲苯磺酰肼 作用下， 以 乙二醇乙醚 为溶剂， 生成 4-Fluor-3'-chlorbibenzyl
  参考文献：
  名称：

  Electronic properties of three-membered rings. II. Transmission of conjugation by the cyclopropane ring

  摘要：

  DOI：

  10.1021/ja01049a012
• 作为产物：
  描述：

  4-氟氯苄 在 sodium hydride 作用下， 以 乙腈 、 苯 为溶剂， 反应 12.0h， 生成 (E)-1-chloro-3-(4-fluorostyryl)benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of some stilbene-based analogues

  摘要：

  The phytoalexin 3,5,4'-trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis(4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum.

  DOI：

  10.1007/s00044-010-9450-y

文献信息

• An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence
  作者：Miles H. Aukland、Fabien J. T. Talbot、José A. Fernández-Salas、Matthew Ball、Alexander P. Pulis、David J. Procter

  DOI：10.1002/anie.201805396

  日期：2018.7.26

  An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp2‐, and

  已经开发了一种中断的Pummerer /镍催化的交叉偶联策略，并将其用于苯乙烯的精制。操作简单的方法可以作为一个锅法进行，涉及直接形成稳定的烯基sulf盐中间体，利用市售的亚砜，催化剂和配体，在环境温度下操作，可容纳sp‐，sp 2‐，和sp 3杂交的有机锌偶联伙伴，并通过两个步骤以高收率提供官能化的苯乙烯产品。中断的Pummerer /环化方法也已用于获得碳和杂环烯基sulf盐进行交叉偶联。
• Nickel-catalyzed tandem conversion of paraformaldehyde : methanol to hydrogen and formate/chemo- and stereoselective hydrogenation of alkynes under neutral conditions
  作者：Murugan Subaramanian、Subarna Sukanya Padhy、Chandrakanth Gouda、Tamal Das、Kumar Vanka、Ekambaram Balaraman

  DOI：10.1039/d3cy01699d

  日期：——

  development of new catalytic protocols for clean and COx-free hydrogen generation from fundamental feedstocks is always interesting and challenging. Herein, we disclose nickel-catalyzed dihydrogen generation from a mixture of paraformaldehyde–methanol under base-free and activator-free conditions. The dihydrogen generation from this redox combination under neutral, oxidative coupling conditions has been

  开发新的催化方案以利用基本原料生产清洁且无CO x的氢气始终是有趣且具有挑战性的。在此，我们公开了在无碱和无活化剂条件下由多聚甲醛-甲醇混合物产生镍催化的氢气。在中性、氧化偶联条件下由这种氧化还原组合产生的氢气已与氢转移反应集成，例如以串联方式对炔烃进行化学和立体选择性氢化。这种前所未有的策略提供了多种高度立体选择性的烯烃，对可还原官能团（如醚、甲硅烷基醚、醛、酮、酯、腈、包括溴和碘基团的卤化物以及杂芳烃）具有优异的耐受性。此外，我们还证明了烯烃在良性条件下的催化立体互变。一些重要的药物生物活性分子的克级规模合成，进一步提高了其合成价值。
• GUPTA, K. C.;NIGAM, R. K.;SRIVASTAVA, NIRUPMA, CURR. SCI., INDIA, 1984, 53, N 4, 191-193
  作者：GUPTA, K. C.、NIGAM, R. K.、SRIVASTAVA, NIRUPMA

  DOI：——

  日期：——
• Electronic properties of three-membered rings. II. Transmission of conjugation by the cyclopropane ring
  作者：R. Garth Pews、N. D. Ojha

  DOI：10.1021/ja01049a012

  日期：1969.10
• Synthesis and biological evaluation of some stilbene-based analogues
  作者：Subhas S. Karki、Santosh R. Bhutle、Ganesh S. Pedgaonkar、P. K. Zubaidha、Rizwan M. Shaikh、Chitra G. Rajput、Girish S. Shendarkar

  DOI：10.1007/s00044-010-9450-y

  日期：2011.11

  The phytoalexin 3,5,4'-trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis(4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum.