(Z)-2,3-bis(4-nitrophenyl)acrylonitrile | 42172-66-7

• 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)-2,3-bis(4-nitrophenyl)acrylonitrile
• 英文别名: 2,3c-bis-(4-nitro-phenyl)-acrylonitrile；2,3c-Bis-(4-nitro-phenyl)-acrylonitril；trans-4-Nitro-α-<4-nitro-phenyl>-zimtsaeure-nitril；trans-4-Nitro-4'-nitro-α-cyanostilben；4.4'-Dinitro-α-cyan-trans-stilben；(Z)-2,3-bis(4-nitrophenyl)prop-2-enenitrile
• CAS: 42172-66-7
• 化学式: C₁₅H₉N₃O₄
• 分子量: 295.254
• InChiKey: QPMLLJYCAKQATA-UKTHLTGXSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  435.7±40.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO: 25mg/mL, pale yellow

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 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：
  115
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 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)-2,3-bis(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

• 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：——
• L'Ecuyer; Olivier, Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 689,691
  作者：L'Ecuyer、Olivier

  DOI：——

  日期：——
• Sulfonic acid functionalized metal–organic framework (S-IRMOF-3): a novel catalyst for sustainable approach towards the synthesis of acrylonitriles
  作者：Ryhan Abdullah Rather、Zeba N. Siddiqui

  DOI：10.1039/c9ra01012b

  日期：——

  A sulfonic acid functionalized metal–organic framework (S-IRMOF-3) has been synthesized by dropwise addition of chlorosulfonic acid (0.5 mL) in IRMOF-3 (1 g) containing 20 mL of CHCl3 at 0 °C under simple stirring. The catalyst was applied in Knoevenagel condensation of various aromatic and hetero-aromatic aldehydes forming acrylonitrile derivatives. The catalyst was characterized thoroughly by using

  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