3-(3-chlorophenyl)-3-chloropropenal | 1224257-72-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-(3-chlorophenyl)-3-chloropropenal
• 英文别名: 3-Chloro-3-(3-chlorophenyl)prop-2-enal
• CAS: 1224257-72-0
• 化学式: C₉H₆Cl₂O
• 分子量: 201.052
• InChiKey: WWBACMISMUDFHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  3-(3-chlorophenyl)-3-chloropropenal 在 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 (E)-2-(3-chlorophenyl)-2-(4,4-bis(4-methoxyphenyl)-1,3-butadienyl)-1,3-dithiane
  参考文献：
  名称：

  路易斯酸通过双 1,3-硫重排促进多取代 1,3-二烯的立体选择性合成

  摘要：

  1,3-二烯是生物活性分子中普遍存在的亚结构，也是合成化学中的多功能构建单元。在此，我们使用路易斯酸促进双 1,3-硫重排，开发了一种直接合成 1,3-二噻吩基取代二烯的方法。该方法能够在温和的反应条件下以高立体选择性和良好的产率合成三取代和四取代的 1,3-二烯。

  DOI：

  10.1002/adsc.202201125
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 3-氯苯乙酮 在 三氯氧磷 作用下， 生成 3-(3-chlorophenyl)-3-chloropropenal
  参考文献：
  名称：

  路易斯酸通过双 1,3-硫重排促进多取代 1,3-二烯的立体选择性合成

  摘要：

  1,3-二烯是生物活性分子中普遍存在的亚结构，也是合成化学中的多功能构建单元。在此，我们使用路易斯酸促进双 1,3-硫重排，开发了一种直接合成 1,3-二噻吩基取代二烯的方法。该方法能够在温和的反应条件下以高立体选择性和良好的产率合成三取代和四取代的 1,3-二烯。

  DOI：

  10.1002/adsc.202201125

文献信息

• Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
  作者：Pawan K. Sharma、Rajiv Kumar、Sita Ram、Navneet Chandak

  DOI：10.1080/00397911.2021.1910846

  日期：2021.6.18

  synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

  摘要 已经描述了使用温和的反应条件，使用经济上良性的碘，氨水和氢氧化钠溶液从易于获得的3-氯丙烯一锅合成β-乙腈。该报告提出了一种便捷，廉价，无毒无害，环保的β-乙腈方法。
• Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity
  作者：Babasaheb P. Bandgar、Sachin A. Patil、Balaji L. Korbad、Shivraj H. Nile、Chandrahase N. Khobragade

  DOI：10.1016/j.ejmech.2010.01.050

  日期：2010.6

  A series of beta-chloro vinyl chalcones have been synthesized by Claisen-Schmidt condensation. beta-chloro vinyl aldehyde has been synthesized by the Vilsmayer-Hack formylation reaction. The structures of the newly synthesized compounds were confirmed by H-1 NMR, IR and Mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-alpha and IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 5a, 5d, 5e, 5g and 5i exhibited promising activity against IL-6 with 58-83% inhibition at 10 mu M concentration None of the compound was found to be cytotoxic in CCK-8 cells at 10 mu M concentration. Whereas compounds 5b, 5d, Se and 5i showed very good antibacterial activity and compounds 5a, 5b, Se and 5i showed good antifungal activity.
• Synthesis and biological screening of a combinatorial library of β-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents
  作者：Babasaheb P. Bandgar、Shrikant S. Gawande

  DOI：10.1016/j.bmc.2009.12.077

  日期：2010.3

  A combinatorial library of beta-chlorovinyl chalcones ( 4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal ( 2) and 1-(2,4-dimethoxyphenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone ( 3) in alkaline conditions furnished the target compound 5-chloro-1-(2,4-dimethoxy-phenyl)-5-phenyl-penta-2,4-dien-1-one ( 4). The synthesized compounds were screened for their biological activity viz. anticancer, anti-inflammatory and antimicrobial activities. Synthesized compounds 4g and 4h revealed promising anti-inflammatory activity (66-67% TNF-alpha and 95-97% IL-6 inhibitory activity at 10 mu M). Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Furthermore, the anticancer activity (30-40%) was shown by compounds 4d, 4e, 4h and 4b at 10 mu M concentrations against ACHN followed by Calu 1, Panc1, HCT116 and H460 cell lines. Some of the compounds 4d, 4e, 4a, 4i and 4b revealed promising antimicrobial activity at MIC 50-100 mu g/mL against selected pathogenic bacteria and fungi. (C) 2010 Published by Elsevier Ltd.