(E)-2,3-双(4-甲氧基苯基)丙烯腈 | 52565-72-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-2,3-双(4-甲氧基苯基)丙烯腈
• 英文名称: (E)-2-(4-methoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile
• 英文别名: 1,2-Di-(4-methoxyphenyl)-acrylnitril；2,3-Bis(4-methoxyphenyl)prop-2-enenitrile；(E)-2,3-bis(4-methoxyphenyl)prop-2-enenitrile
• CAS: 52565-72-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: GGSJIARERFIGST-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2,3-双(4-甲氧基苯基)丙烯腈 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以74%的产率得到2,3-双(4-甲氧基苯基)丙腈
  参考文献：
  名称：

  Discovery of Diarylacrylonitriles as a Novel Series of Small Molecule Sortase A Inhibitors

  摘要：

  On the basis of a hit from random screening, a novel class of small-molecule sortase A inhibitors was generated. The primary structure-activity relationship and the minimal structural requirements for potency were established through structural modifications and molecular modeling studies.

  DOI：

  10.1021/jm0498708
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 吡啶 、 ammonium hydroxide 、 氯化亚砜 、 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (E)-2,3-双(4-甲氧基苯基)丙烯腈
  参考文献：
  名称：

  Discovery of Diarylacrylonitriles as a Novel Series of Small Molecule Sortase A Inhibitors

  摘要：

  On the basis of a hit from random screening, a novel class of small-molecule sortase A inhibitors was generated. The primary structure-activity relationship and the minimal structural requirements for potency were established through structural modifications and molecular modeling studies.

  DOI：

  10.1021/jm0498708

文献信息

• Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C–CN Bond Cleavage and Cyano Transfer
  作者：Hui Chen、Shuhao Sun、Yahu A. Liu、Xuebin Liao

  DOI：10.1021/acscatal.9b04586

  日期：2020.1.17

  methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and non-toxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerance. In hydrocyanation of alkynes, the method

  我们报告镍催化氰化和氢氰化方法分别从芳基卤化物和炔烃制备芳基腈和乙烯基腈。使用廉价且无毒的4-氰基吡啶N-氧化物作为氰基梭，该方法提供了一种在温和且操作简单的反应条件下制备具有宽泛官能团耐受性的芳基氰化物和乙烯基腈的有效方法。在炔烃的氢氰化中，该方法表现出良好的区域选择性，可控方式主要产生E或Z烯基腈，而分别以内部二芳基炔烃和末端炔烃为底物时，则仅产生马尔可夫尼科夫乙烯基腈。
• Ni-Mediated Generation of “CN” Unit from Formamide and Its Catalysis in the Cyanation Reactions
  作者：Luo Yang、Yu-Ting Liu、Yoonsu Park、Sung-Woo Park、Sukbok Chang

  DOI：10.1021/acscatal.8b05111

  日期：2019.4.5

  The in situ generation of a “cyano” unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form “CN” and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases

  从容易获得的有机前体原位产生“氰基”单元在合成化学中引起了极大的兴趣。在此，我们报道了镍介导的甲酰胺脱水形成“ CN”的第一个例子，以及其随后在炔烃的氢氰化和芳基卤化物的氰化中的催化应用。甲酰胺可以作为腈单元的方便来源，因为它会释放水作为唯一的副产物。
• Accelerated Discovery of α-Cyanodiarylethene Photoswitches
  作者：Niklas F. König、Dragos Mutruc、Stefan Hecht

  DOI：10.1021/jacs.1c03631

  日期：2021.6.23

  thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible C═C double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially

  氰基二芳基乙烯发色团能够通过动态共价化学 (DCC) 进行结构交换。在这个过程中，分子支架的中心亚乙基桥可以被破坏，从而能够在重整亚乙基桥周围组装新的芳基部分组合。可逆的 C=C 双键交换已经使用 α-氰基芪进行了示例性的研究。在温和条件下建立 α-氰基二芳基乙烯与芳基乙腈的动态平衡反应是获取具有潜在改进性能的新型光开关结构库的基础。当受到足够波长的光照射时，α-氰基二芳基乙烯会发生Z / E异构化后闭环。通过使用所需的检测波长筛选可访问的动态发色团库，我们可以识别具有三态光致变色的特定二噻吩基类似物。功能发色团的动态结构库与光导筛选和选择相结合，应该会导致对结构多样性染料化学的更快速探索。
• Phenol derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0124369A1

  公开（公告）日：1984-11-07

  A phenol derivative of the formula wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxy- indanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R1 is joined to R2, and wherein X is -CONR2-, -CSNR2-, -NR12CO-, -NR12CS-, -NR12CONR2-, , -SO2NR2-or -CO-, or, when R is not hydrogen, is -NR12COO-, -S-, -SO- or -SO2-, wherein R2 is hydrogen or alkyl, or R1 and R2 together form alkylene; wherein R12 is hydrogen or alkyl, and wherein R22 is hydrogen, cyano or nitro; or a salt thereof when appropriate. The compounds possess antioestrogenic activity and may be used for the treatment of hormone-dependent breast tumours or of anovulatory infertility.

  式中的苯酚衍生物 其中 NU 是定义的双酚核，包括羟基苯基-羟基萘基、羟基苯基-羟基茚基、羟基苯基-羟基苯并噻吩基或二羟基乙烯基或乙烯基核； 其中 A 是亚烷基、亚烯基或亚炔基，可被亚苯基或其他连接物打断、 其中 R1 是氢、或烷基、烯基、环烷基、卤代烷基、芳基或芳烷基，或 R1 与 R2 连接，且其中 X 是-CONR2-、-CSNR2-、-NR12CO-、-NR12CS-、-NR12CONR2-、 ，-SO2NR2-或-CO-，或当 R 不是氢时，是-NR12COO-，-S-，-SO-或-SO2-，其中 R2 是氢或烷基，或 R1 和 R2 一起形成亚烷基； 其中 R12 是氢或烷基，R22 是氢、氰基或硝基； 或其适当的盐。这些化合物具有抗雌激素活性，可用于治疗激素依赖性乳腺肿瘤或无排卵性不孕症。
• Solvent-free condensation of arylacetonitrile with aldehydes
  作者：Régis Guillot、André Loupy、Abdelkrim Meddour、Michèle Pellet、Alain Petit

  DOI：10.1016/j.tet.2005.07.040

  日期：2005.10

  The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110 degrees C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield. (c) 2005 Elsevier Ltd. All rights reserved.