3-(2-methoxyphenyl)-1-(4-nitrophenyl)-prop-2-en-1-one | 39059-97-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-methoxyphenyl)-1-(4-nitrophenyl)-prop-2-en-1-one
• 英文别名: 3-(2-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one
• CAS: 39059-97-7
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: GPTZGDOZQOHFFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  472.7±45.0 °C(Predicted)
• 密度：
  1?+-.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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)-1-(4-nitrophenyl)-prop-2-en-1-one 在 一水合肼 作用下， 以 水 为溶剂， 反应 2.1h， 以88.33%的产率得到
  参考文献：
  名称：

  Biosynthesis of ZrO ₂ for ZrO ₂ @Ag‐S‐CH ₂ COOH as the retrievable catalyst for the one‐pot green synthesis of pyrazoline derivatives and their anticancer evaluation

  摘要：

  AbstractIn the present work,Ficus benghalensisleaf extract was used for the synthesis of ZrO2nanoparticles. Further, ZrO2@Ag‐S‐CH2‐COOH was synthesized using biosynthesized ZrO2, and its catalytic potential was examined in the synthesis of pyrazoline from reaction of chalcone and hydrazine hydrate at room temperature. The structural conformation of ZrO2@Ag‐S‐CH2‐COOH has been done using FT‐IR, SEM, EDX, XRD, TGA‐TDA, XPS, and DLS techniques, high turnover number (TON), and high turnover frequency. The ZrO2@Ag‐S‐CH2‐COOH demonstrated outstanding catalytic activity for the synthesis of pyrazolines. The structures of the pyrazoline derivatives were confirmed by FT‐IR,1H and13C NMR, and mass spectrometry techniques. Synthesized pyrazoline were tested for anticancer activity against human lung cancer cell line A549 study and confirmed by molecular docking investigations.

  DOI：

  10.1002/aoc.6666
• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 对硝基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 3-(2-methoxyphenyl)-1-(4-nitrophenyl)-prop-2-en-1-one
  参考文献：
  名称：

  微波辐射下H3[PW12O40]/SiO2催化一锅法无溶剂合成1,3,5-三取代1H-吡唑

  摘要：

  开发了1,3,5-三取代1 H-吡唑的有效合成方法。使用催化剂 H 3 [ PW 12 O 40 ]/SiO 2在微波辐射和无溶剂条件下（74- 90%) 并通过 HR-MS、FT-IR、1 H NMR 和13进行了表征C 核磁共振波谱。研究发现，二氧化硅对磷钨酸有良好的负载分散作用，能有效吸收微波能促进缩合反应。该方法的优点是反应条件环保、操作简单、底物广泛、收率高、H 3 [PW 12 O 40 ]/SiO 2可重复利用。此外，还给出了化合物1-(4-氯苯基)-5-(2-甲氧基苯基)-3-(4-硝基苯基)-1 H-吡唑在三斜晶系P-1空间群中的晶体结构。 图形概要

  DOI：

  10.1007/s00706-022-02902-2
• 作为试剂：
  描述：

  1,1-二苯-2-苦基肼 在 3-(2-methoxyphenyl)-1-(4-nitrophenyl)-prop-2-en-1-one 作用下， 生成 1,1-二苯基-2-苦味酰肼
  参考文献：
  名称：

  Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

  摘要：

  Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH3 and -OCH3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.

  DOI：

  10.1007/s00044-010-9342-1

文献信息

• Rapid abnormal [3+2]-cycloaddition of isatin <i>N</i>,<i>N</i>′-cyclic azomethine imine 1,3-dipoles with chalcones
  作者：Guizhou Yue、Zhengjie Dou、Zexi Zhou、Li Zhang、Juhua Feng、Huabao Chen、Zhongqiong Yin、Xu Song、Xiaoxia Liang、Xianxiang Wang、Hanbing Rao、Cuifen Lu

  DOI：10.1039/d0nj00887g

  日期：——

  The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2–5 min. The dicyclic spiropyrrolidine oxoindole was smoothly acquired in moderate to excellent yields (35–95%) with high diastereoselectivities (>20 : 1 dr).

  快速报道了新型二环螺吡咯烷的合成，该反应使用取代的靛红和吡唑烷酮与缩醛的缩合反应，在2–5中使用[3 + 2]-靛红N环加成，N'-环偶氮甲亚胺亚胺1,3-偶极。分钟 双环螺吡咯烷氧杂吲哚以中等至优异的收率（35％至95％）平稳地获得，具有非对映选择性高（> 20：1 dr）。
• Synthesis of 1, 3, 5-trisubstituted-4,5-dihydro-1H-pyrazole catalyzed by vitamin B1 and its fluorescence properties
  作者：Dawei Zhang、Lu Ren、Ailing Liu、Yumin Zhang、Yang Lv、Qiang Gu

  DOI：10.1007/s11164-021-04655-9

  日期：2022.3

  Abstract An efficient synthesis of 1,3,5-trisubstituted-1H-pyrazoles was developed via cyclocondensation in 78–92% yields starting from α,β-unsaturated aldehydes/ketones with substituted phenylhydrazine using vitamin B1 as a catalyst, and was characterized by HR-MS, FT-IR, 1H NMR and 13C NMR spectroscopy. The reaction has simple operation, metal-free catalysis, acid or base free catalysis. As a green

  摘要 1,3,5-三取代-1 H-吡唑的高效合成是通过以维生素 B 1为催化剂的α , β-不饱和醛/酮与取代苯肼开始的缩合反应，收率为 78-92% ，并对其进行了表征通过 HR-MS、FT-IR、1 H NMR 和13 C NMR 光谱。该反应操作简单，无金属催化，无酸或碱催化。作为一种绿色催化剂，维生素B 1被发现具有良好的催化活性和缩合反应的可重复使用性。1,3,5-三取代-1 H当吸电子基团与苯乙酮相连时，-吡唑在不同溶剂中呈现橙红色至青色（以化合物5i为例）。化合物5i作为金属离子荧光探针对Ag +检测具有优异的选择性。化合物3-(4-氯苯基)-1,5-二苯基-4,5-二氢-1H-吡唑( 5b )的晶体结构呈正交空间群Pca 21并形成外消旋晶体。 图形概要
• Thiophosphoramide catalyzed asymmetric Michael addition of cyclopentanone to chalcones
  作者：Yunfeng Liu、Yang Wu、Aidang Lu、Youming Wang、Guiping Wu、Zhenghong Zhou、Chuchi Tang

  DOI：10.1016/j.tetasy.2011.02.015

  日期：2011.2

  Thiophosphoramide 1b was found to be an effective bifunctional organocatalyst in the asymmetric Michael reaction of cyclopentanone to various chalcones, affording the corresponding adducts in satisfactory yields with moderate to excellent diastereo- (up to 90/10 dr) and enantioselectivities (up to 92% ee).

  在环戊酮与各种查耳酮的不对称迈克尔反应中，硫代磷酰胺1b被发现是一种有效的双功能有机催化剂，以令人满意的产率提供了相应的加合物，具有中等至优异的非对映体（高达90/10 dr）和对映选择性（高达92％ee） ）。