(Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile | 62297-35-2

• 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)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile
• 英文别名: (Z)-2-(4-nitrophenyl)-3-p-tolylacrylonitrile；2-(4-nitro-phenyl)-3c-p-tolyl-acrylonitrile；2-(4-Nitro-phenyl)-3c-p-tolyl-acrylonitril；4'-Methyl-4-nitro-α-cyan-trans-stilben；(Z)-2-(4-nitrophenyl)-3-(p-tolyl)prop-2-enenitrile；(Z)-3-(4-methylphenyl)-2-(4-nitrophenyl)prop-2-enenitrile
• CAS: 62297-35-2
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: MMSNMLBBZACDIP-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile 生成
  参考文献：
  名称：

  Walkow, F.; Epperlein, J.; Mustroph, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 5, p. 799 - 807

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯甲醛 、 对硝基苯乙腈 在 哌啶 作用下， 生成 (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile
  参考文献：
  名称：

  Patai; Israeli, Bulletin of the Research Council of Israel, 1959, vol. 8, p. 179,183

  摘要：

  DOI：

文献信息

• Harnessing sun for catalyst and sensitizer free regio- and stereo-selective [2+2] cycloaddition
  作者：Kunal Kumar Jha、Sanjay Dutta、Saibal Sar、Subhabrata Sen、Parthapratim Munshi

  DOI：10.1016/j.tet.2018.10.065

  日期：2018.12

  Presence of cyclobutane rings in bioactive natural products makes them a popular synthetic target. Most common strategy for synthesizing cyclobutanes is [2+2] cycloaddition, which is usually facilitated by using ultraviolet radiation and catalysts. Herein we report the design and synthesis of densely functionalized cyclobutanes by alleviating these drawbacks and using sunlight. Further, we identified

  生物活性天然产物中存在环丁烷环，使它们成为受欢迎的合成靶标。合成环丁烷的最常见策略是[2 + 2]环加成反应，通常可通过使用紫外线辐射和催化剂来促进。在本文中，我们通过减轻这些缺点并利用阳光来报告设计和合成致密官能化的环丁烷。此外，我们基于动力学，荧光和晶体学研究确定了可能的转化机制，并评估了产品对MCF7细胞系的生物学活性。烯烃底物的合理设计基于其紫外可见光谱。通过环丁烷的各种类似物的合成阐明了反应的一般方面。进一步，烯烃伙伴的晶体结构和紫外可见光谱有助于我们合理化异二聚体的立体选择性。我们认为，这种节能高效的温和方法将为现有的区域和立体选择性接入环丁烷的策略库做出重大贡献。
• 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.
• Patai; Israeli, Bulletin of the Research Council of Israel, 1959, vol. <A> 8, p. 179,183
  作者：Patai、Israeli

  DOI：——

  日期：——
• Walkow, F.; Epperlein, J.; Mustroph, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 5, p. 799 - 807
  作者：Walkow, F.、Epperlein, J.、Mustroph, H.

  DOI：——

  日期：——