(Z)-3-(4-(dimethylamino)phenyl)-2-(4-methoxyphenyl)acrylonitrile | 6582-06-5

• 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: (Z)-3-(4-(dimethylamino)phenyl)-2-(4-methoxyphenyl)acrylonitrile
• 英文别名: (Z)-3-[4-(dimethylamino)phenyl]-2-(4-methoxyphenyl)acrylonitrile；3c-(4-dimethylamino-phenyl)-2-(4-methoxy-phenyl)-acrylonitrile；3c-(4-Dimethylamino-phenyl)-2-(4-methoxy-phenyl)-acrylonitril；3-(4-(Dimethylamino)phenyl)-2-(4-methoxyphenyl)acrylonitrile；(Z)-3-[4-(dimethylamino)phenyl]-2-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 6582-06-5
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: KBOBWBOCWNTNSX-FOWTUZBSSA-N

物化性质

• 熔点：
  149-151 °C
• 沸点：
  449.4±45.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-(dimethylamino)phenyl)-2-(4-methoxyphenyl)acrylonitrile 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到3-[4-(dimethylamino)phenyl]-2-(4-methoxyphenyl)propanenitrile
  参考文献：
  名称：

  Reduction of .alpha.,.beta.-diarylacrylonitriles by sodium borohydride

  摘要：

  DOI：

  10.1021/jo01289a038
• 作为产物：
  描述：

  对甲氧基苯乙腈 、 对二甲氨基苯甲醛 在 乙醇 、 sodium ethanolate 作用下， 生成 (Z)-3-(4-(dimethylamino)phenyl)-2-(4-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  Unsymmetrical Cyanostilbenes

  摘要：

  DOI：

  10.1021/ja01256a042

文献信息

• 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。
• (<i>Z</i>)-2-(2-Bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An Orally Bioavailable PPARβ/δ-Selective Ligand with Inverse Agonistic Properties
  作者：Sonja Lieber、Frithjof Scheer、Wolfgang Meissner、Simone Naruhn、Till Adhikary、Sabine Müller-Brüsselbach、Wibke E. Diederich、Rolf Müller

  DOI：10.1021/jm2017122

  日期：2012.3.22

  The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor beta/delta (PPAR beta/delta) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator interaction assays to screen 2693 compounds of the Open Chemical Repository of the NCl/NIH Developmental Therapeutics Program for inhibitory PPAR beta/delta ligands. One compound, (Z)-3-(4-dimethylamino-phenyl)-2-phenyl-acrylonitrile, was used for a systematic SAR study. This led to the design of derivative 37, (Z)-2-(2-bromopheny1)-3-[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172), a novel PPAR beta/delta-selective ligand showing high binding affinity (IC50 = 27 nM) and potent inverse agonistic properties. 37 selectively inhibited the agonist-induced activity of PPAR beta/delta, enhanced transcriptional corepressor recruitment, and down-regulated transcription of the PPAR beta/delta target gene Angptl4 in mouse myoblasts (IC50 = 9.5 nM). Importantly, 37 was bioavailable after oral application to mice with peak plasma levels in the concentration range of its maximal inhibitory potency, suggesting that 37 will be an invaluable tool to elucidate the functions and therapeutic potential of PPAR beta/delta.
• Long, Huan-Yuan; Zhang, Jin; Li, Zi-Wei, Journal of the Chemical Society of Pakistan, 2019, vol. 41, # 5, p. 868 - 873
  作者：Long, Huan-Yuan、Zhang, Jin、Li, Zi-Wei、Zhou, Peng、Peng, Tian-Ying、He, Guo-Wen

  DOI：——

  日期：——
• KULP S. S.; CALDWELL C. B., J. ORG. CHEM., 1980, 45, NO 1, 171-173
  作者：KULP S. S.、 CALDWELL C. B.

  DOI：——

  日期：——
• STEWART J. T.; KIM M., J. CHEM. AND ENG. DATA, 32,(1987) N 3, 387-389
  作者：STEWART J. T.、 KIM M.

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