(Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile | 42172-62-3

• 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-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile
• 英文别名: 2-(4-nitro-phenyl)-3c-(4-methoxy-phenyl)-acrylonitrile；2-(4-Nitro-phenyl)-3c-(4-methoxy-phenyl)-acrylonitril；4'-Methoxy-4-nitro-α-cyan-trans-stilben；(Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)prop-2-enenitrile
• CAS: 42172-62-3
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: FJBBWHCHJAMHGD-GXDHUFHOSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  433.8±40.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile 在 sodium hypochlorite 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 42.0h， 生成 2-Cyano-5-(p-methoxyphenyl)-2-(p-nitrophenyl)tetrahydrofuran-3,4-dicarboxylic anhydride
  参考文献：
  名称：

  Clawson, Paul; Whiting, Donald A., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1193 - 1198

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯乙腈 、 4-甲氧基苯甲醛 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 以55%的产率得到(Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile
  参考文献：
  名称：

  简便地制备α-氰基-α，ω-二芳基低聚二亚乙烯基：一类新型的可彩色调谐的固体发射体

  摘要：

  有效的Knoevenagel缩合反应用于构建一系列的α-氰基-α，ω-二芳基寡聚谷氨酰胺，它们在固态下显示出显着的荧光发射。在研究共轭长度对荧光性质的影响时，我们发现二烯结构显示出优异的固态发光。此外，可以通过在末端芳基上引入供体或受体官能团来调节发光颜色。通过向α-氰基-α，ω-二芳基二亚乙烯基部分添加不同的官能团，可以实现可见光区域的全色发射。阐明了结构与属性之间的关系，并讨论了一些观察结果，例如取代位置效应。

  DOI：

  10.1002/asia.201500473

文献信息

• Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water
  作者：Guowei Li、Jia Xiao、Wenqin Zhang

  DOI：10.1039/c2gc35483g

  日期：——

  A series of new fiber catalysts has been synthesized by aminating a commercially available polyacrylonitrile fiber with polyamines such as diethylenetriamine and triethylenetetramine. These fiber catalysts can efficiently catalyze the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate in water (yields: 95–98%). The triethylenetetramine aminated fiber catalyst was used to catalyze the condensations of a wide range of aromatic aldehydes and active methylene compounds and in each case, this catalyst performed well with yields higher than 93%. This fiber catalyst also exhibited excellent reusability (up to 21 times) and photostability.

  通过将市售聚丙烯腈纤维与聚胺（如二亚乙基三胺和三亚乙基四胺）进行胺化，合成了一系列新型纤维催化剂。这些纤维催化剂能高效催化苯甲醛与氰乙酸乙酯在水中进行的Knoevenagel缩合反应（产率：95-98%）。三亚乙基四胺胺化纤维催化剂被用于催化多种芳香醛与活性甲基化合物之间的缩合反应，并且每种情况下，该催化剂都表现出色，产率均高于93%。此纤维催化剂还具有优异的重复使用性（可达21次）和光稳定性。
• 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。
• Sonocrystallization of CMONS Needles and Nanocubes: Mechanistic Studies and Advanced Crystallinity Characterization by Combining X-ray and Electron Diffractions with DNP-Enhanced NMR
  作者：Xavier Cattoën、Akshay Kumar、Fabien Dubois、Carole Vaillant、Mauricio Matta-Seclén、Olivier Leynaud、Stéphanie Kodjikian、Sabine Hediger、Gaël De Paëpe、Alain Ibanez

  DOI：10.1021/acs.cgd.1c01246

  日期：2022.4.6

  of two distinct crystalline phases for different diastereomers. The crystallinity of CMONS needles was probed by various techniques, including X-ray and electron diffractions, fluorescence spectroscopy, and dynamic nuclear polarization (DNP)-enhanced solid-state nuclear magnetic resonance. The latter was used to hyperpolarize 1H nuclei and to record 1H-13C and 1H-15N CPMAS NMR spectra at natural isotopic

  本研究介绍了一种由超声波辅助的新纳米结晶方法，该方法可产生 CMONS（一种二苯乙烯染料）的针状或纳米立方体，对多晶型和窄尺寸分布具有出色的控制。由于通过高强度超声从溶解的分子氧中产生自由基，在没有氮气鼓泡的情况下观察到反式到顺式异构化，形成不同的非对映异构体的两个不同的结晶相。通过各种技术探测 CMONS 针的结晶度，包括 X 射线和电子衍射、荧光光谱和动态核极化 (DNP) 增强型固态核磁共振。后者用于超极化1 H 核并记录1天然同位素丰度下的H- 13 C 和1 H- 15 N CPMAS NMR 光谱，具有非常高的信噪比。有了这样的灵敏度，人们可以轻松地区分 CMONS 的顺式和反式 I形式，检测多个多晶相的存在（即使贡献很小），并检查无定形相的存在。最后，在使用 CTAB 表面活性剂稳定中间纳米立方体对抗 Ostwald 成熟和有序聚集机制后，确定了 CMONS 针形成的机制。
• 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：——