(2Z)-3-[4-(二甲氨基)苯基]-2-苯基丙-2-烯腈 | 1222-61-3

• 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: (2Z)-3-[4-(二甲氨基)苯基]-2-苯基丙-2-烯腈
• 英文名称: (Z)-3-(4-(dimethylamino)phenyl)-2-phenylacrylonitrile
• 英文别名: 3-(4-(Dimethylamino)phenyl)-2-phenylacrylonitrile；(Z)-3-[4-(dimethylamino)phenyl]-2-phenylprop-2-enenitrile
• CAS: 1222-61-3
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: HYAJIHDALOHMPT-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (2Z)-3-[4-(二甲氨基)苯基]-2-苯基丙-2-烯腈 在 乙醇 、 镍 、 乙酸乙酯 作用下， 40.0 ℃ 、9.81 MPa 条件下， 生成 bis-[3-(4-dimethylamino-phenyl)-2-phenyl-propyl]-amine
  参考文献：
  名称：

  Über对二甲基氨基苯甲酮II。Zur Kenntnis der auxochromen Gruppen

  摘要：

  DOI：

  10.1002/hlca.19310140618
• 作为产物：
  描述：

  苯乙腈 、 对二甲氨基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以95%的产率得到(2Z)-3-[4-(二甲氨基)苯基]-2-苯基丙-2-烯腈
  参考文献：
  名称：

  基于α-氰基二苯乙烯的荧光团：聚集诱导的增强发射，溶剂致变色和pH效应†

  摘要：

  合成了一系列被二甲基苯胺，二苯基苯胺和咔唑取代的α-氰基对苯二酚，并研究了它们在均相溶剂，二恶烷-水二元混合物和固态下的光谱性质。Stilbenes（1和4）在均相溶剂中显示出较弱的发射行为，但在水和固态中显示出显着的红移发射以及增强的强度。这种现象是由于聚集引起的增强的发射效应。其他对苯二酚在水和固态中也表现出显着的溶剂变色发光行为，并具有类似的增强发光特性。发射对酸性或碱性强度变化的敏感性确定了这些分子作为荧光探针的实用性。

  DOI：

  10.1039/c4nj01103a

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。
• Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents
  作者：Mohammad Sayed Alam、Young-Joo Nam、Dong-Ung Lee

  DOI：10.1016/j.ejmech.2013.08.031

  日期：2013.11

  In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or pnitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Merckx, Bulletin des Societes Chimiques Belges, 1949, vol. 58, p. 460,468
  作者：Merckx

  DOI：——

  日期：——
• Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
  作者：Amreen K. Bains、Yadav Ankit、Debashis Adhikari

  DOI：10.1021/acs.orglett.1c00162

  日期：2021.3.19
• Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases
  作者：Bosco A. D'Sa、Philip Kisanga、John G. Verkade

  DOI：10.1021/jo972343u

  日期：1998.6.1

  We report herein the use of 3-30 mol % of a new class of tricyclic strong nonionic Lewis bases P(MeNCH2CH2)(3)N and P(HNCH2CH2)(i-PrNCH2CH2)(2)N for the direct catalytic synthesis of a variety of functionalized alpha,beta-unsaturated nitriles in high yields from aldehydes and acetonitrile or benzyl cyanide at 40-50 degrees C. Evidence for a novel mechanistic pathway proposed for this reaction in a polar protic solvent such as methanol, and a nonpolar aprotic solvent such as benzene is also presented. Under these conditions, primary and secondary aliphatic aldehydes do not condense satisfactorily with acetonitrile to give the alpha,beta-unsaturated nitrile, and ketones do not condense with either benzyl cyanide or acetonitrile.

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