(Z)-3-(4-chlorophenyl)-2-(4-nitrophenyl)acrylonitrile | 42172-64-5

• 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-chlorophenyl)-2-(4-nitrophenyl)acrylonitrile
• 英文别名: 3c-(4-chloro-phenyl)-2-(4-nitro-phenyl)-acrylonitrile；3c-(4-Chlor-phenyl)-2-(4-nitro-phenyl)-acrylonitril；3-(p-Chlorophenyl)-2-(p-nitrophenyl)acrylonitrile；(Z)-3-(4-chlorophenyl)-2-(4-nitrophenyl)prop-2-enenitrile
• CAS: 42172-64-5
• 化学式: C₁₅H₉ClN₂O₂
• 分子量: 284.702
• InChiKey: RGRMXCOYMYLJMX-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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)-3-(4-chlorophenyl)-2-(4-nitrophenyl)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：

  4-氯苯甲醛 、 对硝基苯乙腈 在 sulfonic acid functionalized zinc(2-aminoterephthalate) metal organic framework 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以96%的产率得到(Z)-3-(4-chlorophenyl)-2-(4-nitrophenyl)acrylonitrile
  参考文献：
  名称：

  磺酸功能化金属有机骨架 (S-IRMOF-3)：一种新型催化剂，用于合成丙烯腈的可持续方法†

  摘要：

  磺酸功能化金属有机骨架 (S-IRMOF-3) 通过在简单搅拌下在 0 °C 下将氯磺酸 (0.5 mL) 滴加到含有 20 mL CHCl 3的 IRMOF-3 (1 g) 中合成。该催化剂应用于各种芳香醛和杂芳香醛的 Knoevenagel 缩合反应，形成丙烯腈衍生物。采用FT-IR、XRD、13 C MAS NMR、SEM、EDX、元素映射、TEM、BET、NH 3 -TPD和TGA/DTA技术对催化剂进行了全面表征。在 FT-IR 光谱中，在 1694 cm -1、1254–769 cm -1和 1033 cm -1处存在特征带，在 XRD 图案中存在 2 θ ≃ 6.7° 和 9.8° 以及δ= 31.79, 39.55, 129.61, 131.46 (4C, CH), 133.54, 140.07 (2C), 167.71, 171.47 ppm (2C, 2C O) 在固态13

  DOI：

  10.1039/c9ra01012b

文献信息

• Bisazo-benzofuran compounds, their use as charge carrier generating compounds and intermediates for their preparation
  申请人：SHARP KABUSHIKI KAISHA

  公开号：EP0780363A1

  公开（公告）日：1997-06-25

  There is provided an electrophotographic photoconductor comprising as a charge carrier generating substance a bisazo compound of the general formula (I): wherein R1 and R2 are the same or different, each representing a hydrogen atom, a halogen atom, a lower alkyl group optionally substituted with a fluorine atom, an aralkyl group optionally having a substituent, a lower alkoxy group, or a di-(lower alkyl)amino group; n is an integer from 1 to 3; m is an integer from 1 to 4; and Cp1 and Cp2 are the same or different, each representing an aromatic condensed heterocyclic or aromatic condensed hydrocarbon residue having at least one phenolic hydroxyl group and optionally having a substituted carbamoyl group or a heterocyclic group.

  本发明提供了一种电子照相光电导体，该光电导体包含通式（I）的双偶氮化合物作为电荷载体生成物质： 其中 R1 和 R2 相同或不同，各自代表氢原子、卤素原子、任选被氟原子取代的低级烷基、任选具有取代基的芳烷基、低级烷氧基或二(低级烷基)氨基；n 是 1 至 3 的整数；m 是 1 至 4 的整数；以及 Cp1 和 Cp2 相同或不同，各自代表芳香缩合杂环或芳香缩合烃残基，该残基具有至少一个酚羟基，并可选具有取代的氨基甲酰基或杂环基。
• Pfeiffer et al., Journal fur praktische Chemie (Leipzig 1954), 1929, vol. <2> 121, p. 86,90
  作者：Pfeiffer et al.

  DOI：——

  日期：——
• 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：——
• Bisazo-benzofuran compounds, their use as charge carrier generating compounds
  申请人：SHARP KABUSHIKI KAISHA

  公开号：EP0780363B1

  公开（公告）日：2001-09-26