(E)-3-[5-(4-Chloro-phenyl)-furan-2-yl]-1-p-tolyl-propenone | 294635-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3-[5-(4-Chloro-phenyl)-furan-2-yl]-1-p-tolyl-propenone
• 英文别名: 3-[5-(4-Chlorophenyl)furan-2-yl]-1-(4-methylphenyl)prop-2-en-1-one
• CAS: 294635-98-6
• 化学式: C₂₀H₁₅ClO₂
• 分子量: 322.791
• InChiKey: ABBANFLTRRYSBR-UHFFFAOYSA-N

物化性质

• 沸点：
  487.4±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-[5-(4-Chloro-phenyl)-furan-2-yl]-1-p-tolyl-propenone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 1-[3-[5-(4-Chlorophenyl)furan-2-yl]-5-(4-methylphenyl)-3,4-dihydropyrazol-2-yl]ethanone
  参考文献：
  名称：

  Studies on arylfuran derivatives

  摘要：

  Arylfurylpropenones 3 were synthesized by Claisen-Schmidt condensation of arylfurfurals 1 with various substituted acetophenones 2. Cyclocondensation of these arylfurylpropenones 3 with hydrazine hydrate and phenylhydrazine furnished 1H-pyrazolines 4 and N-phenylpyrazolines 6, respectively. In order to study the structure-activity relationships, pyrazolines 4 were converted into their N-acetyl derivatives 5. The antibacterial properties of the new pyrazoline derivatives were studied.

  DOI：

  10.1016/s0014-827x(00)00030-6
• 作为产物：
  描述：

  5-(4-氯苯基)-2-呋喃甲醛 、 对甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-3-[5-(4-Chloro-phenyl)-furan-2-yl]-1-p-tolyl-propenone
  参考文献：
  名称：

  MCF-7 Human Breast Adenocarcinoma Anticancer and Antimicrobial, in silico Docking and ADME Prediction Studies of Furan Moiety Containing Substituted 2-Aminopyrimidine Derivatives

  摘要：

  一系列4-(5-(4-氯苯基)呋喃-2-基)-6-苯基嘧啶-2-胺衍生物（5a-h）是通过将2-(4-氯苯基)-5-苯乙烯基呋喃（3a-h）与硝酸胍在绝对乙醇中进行常规方法合成的，并对其进行了体外抗癌、抗微生物活性和体内研究评估。含有取代氨基嘧啶的呋喃基结构衍生物（5a-h）的化学结构是通过红外、1H和13C NMR光谱数据以及CHN分析阐明的。通过细菌蛋白1UAG预测了合成化合物（5a-h）的体外对接研究，并对合成化合物（5a-h）进行了体外ADME预测。通过MMT测定法对化合物5b进行了体外抗癌研究。化合物5b显示LC50值为120.15 ± 0.003 μg/mL。通过不同菌株筛选了化合物（5a-h）的体外抗微生物活性。化合物5h在苯环对位取代有电子吸引基团的情况下表现出良好的抗微生物活性，针对所有细菌菌株和真菌菌株。在体外研究中，化合物5h的对接得分（-9.7 kcal/mol）优于环丙沙星（-7.8 kcal/mol）。

  DOI：

  10.14233/ajchem.2021.23186

文献信息

• Study of Regiochemical Trends During the Synthesis of Furan and 5-(<i>p</i>-chlorophenyl)Furan Containing Novel Spiropyrrolidine Library Through 1,3-dipolar Cycloaddition Reactions
  作者：Sahana Mallya、Balakrishna Kalluraya、H. S. Vidyashree Jois

  DOI：10.1002/jhet.2499

  日期：2016.11

  A new class of functionalized furan and 5‐(p‐chlorophenyl)furan containing spiropyrrolidines has been synthesized in moderate to excellent yields by the one‐pot, three‐component 1,3‐dipolar cycloaddition reaction of in situ generated azomethine ylides with various furan/aryl furan‐substituted chalcones as dipolarophiles. The effect of electron deficient substituents at the fifth position of the furan

  通过一锅，三组分，1,3-偶极环加成反应原位生成的偶氮甲亚胺与各种呋喃已合成了新型的功能化呋喃和含有螺吡咯烷的5-（对氯苯基）呋喃/芳基呋喃取代的查耳酮类化合物为双极性亲和剂。研究了查尔酮中呋喃环第五位的缺电子取代基对形成的环加成反应的区域化学的影响。通过分析和光谱数据证明了新合成的环瘾者的结构。
• Studies on arylfuran derivatives
  作者：B Shivarama Holla、P.M Akberali、M.K Shivananda

  DOI：10.1016/s0014-827x(00)00030-6

  日期：2000.4

  Arylfurylpropenones 3 were synthesized by Claisen-Schmidt condensation of arylfurfurals 1 with various substituted acetophenones 2. Cyclocondensation of these arylfurylpropenones 3 with hydrazine hydrate and phenylhydrazine furnished 1H-pyrazolines 4 and N-phenylpyrazolines 6, respectively. In order to study the structure-activity relationships, pyrazolines 4 were converted into their N-acetyl derivatives 5. The antibacterial properties of the new pyrazoline derivatives were studied.
• MCF-7 Human Breast Adenocarcinoma Anticancer and Antimicrobial, in silico Docking and ADME Prediction Studies of Furan Moiety Containing Substituted 2-Aminopyrimidine Derivatives
  作者：Manju Mathew、Muthuvel Ramanathan Ezhilarasi

  DOI：10.14233/ajchem.2021.23186

  日期：——

  A series of 4(5-(4-chlorophenyl)furan-2-yl)-6-phenylpyrimidin-2-amine derivatives (5a-h) were synthesized from 2-(4-chlorophenyl)-5-styrylfuran (3a-h) with guanidine nitrate in absolute ethanol under conventional method and evaluated for their in vitro anticancer, antimicrobial activities and in silico studies. The chemical structure of the furan moiety containing substituted amino pyrimidine derivatives (5a-h) were elucidated from spectroscopic analysis like infrared, 1H & 13C NMR spectral data and CHN analysis. in silico docking studies were predicted for the synthesized compounds (5a-h) using bacterial protein 1UAG and in silico ADME predictions were also carried for the synthesized compounds (5a-h). The in vitro anticancer study was carried the compound 5b by MMT assay. Compound 5b shows the LC50 value of 120.15 ± 0.003 μg/mL. in vitro Antimicrobial activities were screened for the compounds (5a-h) using different strains. Compound 5h has electron withdrawing group in benzene ring substituted in the para position showed good antimicrobial activity against all the bacterial strains and fungal strains. in silico studies, compound 5h shows excellent docking score (-9.7 kcal/mol) compared with ciprofloxacin (-7.8 kcal/mol).

  一系列4-(5-(4-氯苯基)呋喃-2-基)-6-苯基嘧啶-2-胺衍生物（5a-h）是通过将2-(4-氯苯基)-5-苯乙烯基呋喃（3a-h）与硝酸胍在绝对乙醇中进行常规方法合成的，并对其进行了体外抗癌、抗微生物活性和体内研究评估。含有取代氨基嘧啶的呋喃基结构衍生物（5a-h）的化学结构是通过红外、1H和13C NMR光谱数据以及CHN分析阐明的。通过细菌蛋白1UAG预测了合成化合物（5a-h）的体外对接研究，并对合成化合物（5a-h）进行了体外ADME预测。通过MMT测定法对化合物5b进行了体外抗癌研究。化合物5b显示LC50值为120.15 ± 0.003 μg/mL。通过不同菌株筛选了化合物（5a-h）的体外抗微生物活性。化合物5h在苯环对位取代有电子吸引基团的情况下表现出良好的抗微生物活性，针对所有细菌菌株和真菌菌株。在体外研究中，化合物5h的对接得分（-9.7 kcal/mol）优于环丙沙星（-7.8 kcal/mol）。