1,3-bis(2,4-dichlorophenyl)prop-2-en-1-one | 19738-92-2

• 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: 1,3-bis(2,4-dichlorophenyl)prop-2-en-1-one
• 英文别名: 1,3-di-(2,4-dichlorophenyl)propenone；2,4,2',4'-Tetrachlor-chalcon
• CAS: 19738-92-2
• 化学式: C₁₅H₈Cl₄O
• 分子量: 346.04
• InChiKey: GLTVNVIHTHMZTN-UHFFFAOYSA-N

物化性质

• 沸点：
  483.3±45.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 2,4-二氯苯乙酮 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到1,3-bis(2,4-dichlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  超声介导的10秒钟合成查耳酮作为潜在的法呢基转移酶抑制剂。

  摘要：

  在使用超声探针将（杂）芳基酮和（杂）芳基醛进行克莱森-施密特缩合反应之后，可以轻松快速地合成各种查耳酮和衍生物。与经典的磁力搅拌实验进行了比较，并进行了优化研究，表明氢氧化锂是所研究缩合物的最佳碱性催化剂。还分离了反应的副产物（β-羟基酮，二酮和环己醇）。在体外评估所有化合物抑制人法呢基转移酶的能力，后者是一种与癌症和罕见疾病有关的蛋白质，在NCI-60癌细胞系中也有。分子对靶蛋白具有抑制活性，对不同细胞系具有抑制细胞的作用，对MCF7乳腺癌细胞具有特定的活性。

  DOI：

  10.1016/j.bmcl.2020.127149

文献信息

• Synthesis and antifungal activity of chalcone derivatives
  作者：Yuanyuan Zheng、Xuesong Wang、Sumei Gao、Min Ma、Guiming Ren、Huabing Liu、Xiaohong Chen

  DOI：10.1080/14786419.2015.1007973

  日期：2015.10.2

  In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifungal activity against Sclerotinia sclerotiorum, Helminthosprium maydis, Botrytis cinerea, Rhizoctonia solani and Gibberella zeae. Among them, the inhibition of growth for compound 30 against S. sclerotiorum showed 89.9%, with the median effective concentrations (EC50) of 15.4gmL(-1). The inhibition of growth for compounds 28, 29 and 30 at a concentration of 100gmL(-1) against H. maydis is 90.3%, 90.7% and 91.1%, with EC50 of 15.1, 18.3 and 18.1gmL(-1), respectively.
• Design, Synthesis, and Bioactivities Screening of a Diaryl Ketone-Inspired Pesticide Molecular Library as Derived from Natural Products
  作者：Hong Zhang、Hong Jin、Lan-zhu Ji、Ke Tao、Wei Liu、Hao-yu Zhao、Tai-ping Hou

  DOI：10.1111/j.1747-0285.2011.01082.x

  日期：2011.7

  Three natural products, 1,5‐diphenylpentan‐1‐one, 1,5‐diphenylpent‐2‐en‐1‐one, and 3‐hydroxy‐1,5‐diphenylpentan‐1‐one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as ‘pharmacophores’, a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)‐1‐(2,4‐dichlorophenyl)‐3‐(furan‐2‐yl)‐ ‐prop‐2‐en‐1‐one (III2) was 1.20 mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
• Ultrasounds-mediated 10-seconds synthesis of chalcones as potential farnesyltransferase inhibitors
  作者：Germain Homerin、Adrian Sorin Nica、Amaury Farce、Joëlle Dubois、Alina Ghinet

  DOI：10.1016/j.bmcl.2020.127149

  日期：2020.6

  synthesized, following Claisen-Schmidt condensation of (hetero)aryl ketones and (hetero)aryl aldehydes using a ultrasound probe. A comparison was made with classical magnetic stirring experiments, and an optimization study was realized, showing lithium hydroxide to be the best basic catalyst of the studied condensations. By-products of the reactions (β-hydroxy-ketone, diketones, and cyclohexanols) were also

  在使用超声探针将（杂）芳基酮和（杂）芳基醛进行克莱森-施密特缩合反应之后，可以轻松快速地合成各种查耳酮和衍生物。与经典的磁力搅拌实验进行了比较，并进行了优化研究，表明氢氧化锂是所研究缩合物的最佳碱性催化剂。还分离了反应的副产物（β-羟基酮，二酮和环己醇）。在体外评估所有化合物抑制人法呢基转移酶的能力，后者是一种与癌症和罕见疾病有关的蛋白质，在NCI-60癌细胞系中也有。分子对靶蛋白具有抑制活性，对不同细胞系具有抑制细胞的作用，对MCF7乳腺癌细胞具有特定的活性。