(Z)-3-(2-Nitrophenyl)-2-phenylacrylsaeurenitril | 136036-43-6

• 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-(2-Nitrophenyl)-2-phenylacrylsaeurenitril
• 英文别名: (Z)-2-phenyl-3-(2-nitrophenyl)acrylonitrile；(Z)-3-(2-nitrophenyl)-2-phenylacrylonitrile；3c-(2-nitro-phenyl)-2-phenyl-acrylonitrile；3c-(2-Nitro-phenyl)-2-phenyl-acrylonitril；2-Phenyl-3c-(2-nitro-phenyl)-acrylonitril；(o-Nitrobenzylidene)phenylacetonitrile；(Z)-3-(2-nitrophenyl)-2-phenylprop-2-enenitrile
• CAS: 136036-43-6
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: QKDHOOPDLFPJKV-GXDHUFHOSA-N

物化性质

• 熔点：
  125-126 °C(Solv: ethanol (64-17-5))
• 沸点：
  413.4±40.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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-(2-Nitrophenyl)-2-phenylacrylsaeurenitril 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以98.2%的产率得到2-phenyl-3-(2-nitrophenyl)propionitrile
  参考文献：
  名称：

  通过直接分子内还原性闭环方便地合成1,2,3,4-四氢喹啉

  摘要：

  据报道，一种简单而方便的合成3-芳基-1,2,3,4-四氢喹啉的方法。3-芳基1,2,3,4-四氢喹啉是通过2-苯基-3-（2-硝基苯基）-丙腈衍生物的还原性闭环以中等至高收率直接获得的。

  DOI：

  10.1016/j.tetlet.2006.07.144
• 作为产物：
  描述：

  苯乙腈 、 邻硝基苯甲醛 在 sodium 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以92%的产率得到(Z)-3-(2-Nitrophenyl)-2-phenylacrylsaeurenitril
  参考文献：
  名称：

  通过直接分子内还原性闭环方便地合成1,2,3,4-四氢喹啉

  摘要：

  据报道，一种简单而方便的合成3-芳基-1,2,3,4-四氢喹啉的方法。3-芳基1,2,3,4-四氢喹啉是通过2-苯基-3-（2-硝基苯基）-丙腈衍生物的还原性闭环以中等至高收率直接获得的。

  DOI：

  10.1016/j.tetlet.2006.07.144

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.
• Antiretroviral Therapy for HIV: Drug Resistance and Sequencing
  作者：Wayne S. Burkle

  DOI：10.1016/s1055-3290(06)60243-4

  日期：2002.1
• Synthese substituierter 2-Aminochinolin-1-oxide durch reduktive Cyclisierung substituierter 3-(2-Nitrophenyl)acrylnitrile
  作者：D. Sicker、H. Wilde

  DOI：10.1002/prac.19923340114

  日期：——

  An approach to the class of 2-aminoquinoline-1-oxides is given based on reductive cyclization of appropriate substituted 3-(2-nitrophenyl)acrylonitriles. Thus, 2-nitrobenzylidene compounds 1a - d have been reductively cyclized by H-2/PtO2 or H-2/Pd-C under normal conditions to form N-oxides 2a - d. H-1-NMR data show that 1d has to be regarded as ethyl(Z)-2-cyano-3-hydroxy-3-(2-nitrophenyl)acrylate.The analogous (2-nitrobenzoyl)acetonitrile 3, however, did not cyclize under the same conditions, but yielded anthraniloylacetonitrile 4. The results are discussed in comparison with the reaction behaviour of structural related nitronitriles under comparable conditions. A short survey of reactions leading to heterocyclic N-oxides by reductive cyclization of nitro compounds is given.
• Petrow et al., Journal of the Chemical Society, 1943, p. 316
  作者：Petrow et al.

  DOI：——

  日期：——
• Bauer, Chemische Berichte, 1938, vol. 71, p. 2226,2228
  作者：Bauer

  DOI：——

  日期：——