N-(4-cinnamoylphenyl)benzenesulfonamide | 109171-57-5

• 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: N-(4-cinnamoylphenyl)benzenesulfonamide
• 英文别名: N-[4-(3-phenylprop-2-enoyl)phenyl]benzenesulfonamide
• CAS: 109171-57-5
• 化学式: C₂₁H₁₇NO₃S
• 分子量: 363.437
• InChiKey: LLMDUEDPHNHSGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C(Solv: ethanol (64-17-5))
• 沸点：
  562.3±60.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-cinnamoylphenyl)benzenesulfonamide 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以68%的产率得到N-[4-(5-Phenyl-isoxazol-3-yl)-phenyl]-benzenesulfonamide
  参考文献：
  名称：

  一些带有磺酰胺部分的新型氰基吡啶、异恶唑、吡唑和嘧啶的合成和抗菌活性

  摘要：

  对氨基苯乙酮 1 与对取代苯磺酰氯 2a、b 在吡啶中反应得到对乙酰基衍生物 3a、b，然后与芳醛缩合得到相应的查耳酮 4a-f。后面的查耳酮与丙二腈缩合得到氰基吡啶 5a-f，查耳酮 4a-f 与盐酸羟胺反应得到异恶唑 6a-f，而查耳酮与水合肼缩合得到吡唑啉衍生物 7、8。尿素或硫脲与查耳酮 4b 反应生成嘧啶衍生物 9、10。磺酰氯 2a、b 与对氨基二苯甲酮反应生成对 [(苯磺酰基)酰氨基]二苯甲酮 11a、b，然后与水合肼缩合得到相应的腙衍生物 12a、b。

  DOI：

  10.1080/10426500307933
• 作为产物：
  描述：

  苯磺酰氯 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-(4-cinnamoylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Cascade Michael-Aldol reaction: efficient annulation of sulfonamide chalcones into novel cyclohexenones under solvent-free conditions

  摘要：

  A simple, convenient and efficient synthesis of novel sulfonamide cyclohexenones from differently substituted sulfonamide chalcones has been developed. Syntheses of cyclohexenones have been achieved via cascade Michael-Aldol reaction under solvent free condition. This process features mild and solvent-free synthesis of the titled compounds with high yields (18 examples, up to 95% yield). The synthesized scaffold is a promising intermediate for the further transformation into various heterocyclic compounds.

  DOI：

  10.3998/ark.5550190.p009.488

文献信息

• Synthesis, anti-inflammatory and antioxidant activity of ring-A-monosubstituted chalcone derivatives
  作者：Hiba Iqbal、Visakh Prabhakar、Atul Sangith、Baby Chandrika、Ranganathan Balasubramanian

  DOI：10.1007/s00044-014-1007-z

  日期：2014.10

  A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (H-1 NMR, C-13 NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4'-cyanochalcone 4b also seemed to possess decent antioxidant potential.
• Upadhyay; Dave; Parekh, Journal of the Indian Chemical Society, 1991, vol. 68, # 7, p. 413 - 414
  作者：Upadhyay、Dave、Parekh

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  日期：——
• Jamode; Chandak; Bhagat, Journal of the Indian Chemical Society, 2008, vol. 85, # 11, p. 1169 - 1173
  作者：Jamode、Chandak、Bhagat

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