(E)-N-(3-fluorobenzylidene)-4-methylbenzenesulfonamide | 951762-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-(3-fluorobenzylidene)-4-methylbenzenesulfonamide
• 英文别名: N-(3-Fluorobenzylidene)-4-methylbenzenesulfonamide；(NE)-N-[(3-fluorophenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 951762-68-8
• 化学式: C₁₄H₁₂FNO₂S
• 分子量: 277.319
• InChiKey: GPHVYIHBOVNROJ-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-丁二烯酸 、 (E)-N-(3-fluorobenzylidene)-4-methylbenzenesulfonamide 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 三丁基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 6-(3-fluorophenyl)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid
  参考文献：
  名称：

  Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I

  摘要：

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.

  DOI：

  10.1021/ja070274n
• 作为产物：
  描述：

  对甲苯磺酰胺 在 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 生成 (E)-N-(3-fluorobenzylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  通过机械化学从苯甲醇衍生物和亚氨基碘烷中无金属合成 N-磺酰亚胺

  摘要：

  据报道，通过在球磨设备 (RETSCH 400™) 中使亚氨基碘与大量芳基/杂芳基苯甲醇在 5 mL 的球磨设备 (RETSCH 400™) 中反应，实现了芳基/杂芳基 N-磺酰亚胺的方便且操作方便的机械化学合成。不锈钢（SS）反应罐。CHCl 3 ( η = 0.2–0.4 μL mg -1 ) 用作液体辅助研磨（LAG）辅助剂。这种使用标称量溶剂（如 LAG）的无金属催化剂和无碱合成证明了亚氨基碘烷的有效N-磺酰基转移反应，以中等至良好的产率提供所需的化合物。取代N-磺酰亚胺作为独立的天然产物结构单元和药物中间体以及磺酰胺的前体至关重要，磺酰胺已参与许多治疗计划中潜在的小分子治疗。基于控制反应和 DFT 计算讨论了假定的转化机制。

  DOI：

  10.1039/d3ob00791j

文献信息

• Synthesis and biological evaluation of substituted phenyl azetidine-2-one sulphonyl derivatives as potential antimicrobial and antiviral agents
  作者：Milan Kumar Mandal、Swagatika Ghosh、Hans Raj Bhat、Lieve Naesens、Udaya Pratap Singh

  DOI：10.1016/j.bioorg.2020.104320

  日期：2020.11

  showed good inhibitory activity against fungal strains whereas other derivatives had mild or diminished activity in comparison with standard drug clotrimazole. The antimicrobial study indicated that compounds having electron-withdrawing groups showed the highest activity. Interestingly, these tested compounds showed weak antiviral activity against Vaccinia virus, Human Coronavirus (229E), Reovirus-1

  在本研究中，我们打算合成一系列新颖的取代苯基氮杂环丁烷-2-酮磺酰基衍生物。筛选了整套衍生物5（at）的体外抗菌和抗真菌活性，并进一步筛选了其中的11种化合物的抗病毒活性，以预测其对抗病原体病毒的功效。有趣的是，与氨苄青霉素（标准品）相比，化合物5d，5e，5f，5h，5i和5j表现出相似或更好的抗菌活性。此外，化合物5h，5i，5j和5q与标准药物克霉唑相比，对真菌菌株具有良好的抑制活性，而其他衍生物的活性较弱或减弱。抗菌研究表明，具有吸电子基团的化合物显示出最高的活性。有趣的是，这些测试的化合物在HEL细胞，Vero细胞和MDCK细胞培养物中对牛痘病毒，人冠状病毒（229E），呼肠孤病毒1，辛德比斯病毒，柯萨奇病毒B4，黄热病病毒和乙型流感病毒显示弱的抗病毒活性。本研究的发现可能会开辟新途径，以针对人类致病的致命微生物和病毒。
• Highly Regio- and Stereoselective [3+2] Cycloaddition of Carbonyl Ylides with Imines: A Novel Entry to Oxa-Bridged Piperidinone Ring Systems
  作者：Sengodagounder Muthusamy、Janagiraman Krishnamurthi、Eringathodi Suresh

  DOI：10.1055/s-2005-921891

  日期：——

  The reaction of α-diazo ketones and N-tosylimines in the presence of a rhodium(II) acetate catalyst led diastereoselectively to the oxa-bridged piperidinone ring systems. The stereochemistry was assigned bused on a single-crystal X-ray analysis.

  在醋酸铑 (II) 催化剂存在下，α-重氮酮和 N-甲苯磺酰亚胺的反应非对映选择性地导致氧杂桥接哌啶酮环系统。立体化学被指定用于单晶 X 射线分析。
• Asymmetric catalytic aza-Morita–Baylis–Hillman reaction using chiral bifunctional phosphine amides as catalysts
  作者：Ming-Juan Qi、Teng Ai、Min Shi、Guigen Li

  DOI：10.1016/j.tet.2007.11.039

  日期：2008.2

  The asymmetric catalytic aza-Morita–Baylis–Hillman reaction of N-sulfonated imines with α,β-unsaturated ketones has been successfully conducted by using chiral bifunctional phosphine amides as catalysts. A series of new chiral bifunctional phosphine amides were designed, synthesized, and systematically studied for this asymmetric reaction. The corresponding aza-MBH adducts were obtained in good yields

  N-磺化亚胺与α，β-不饱和酮的不对称催化氮杂-Morita-Baylis-Hillman反应已通过使用手性双官能膦酰胺作为催化剂成功进行。针对该不对称反应，设计，合成和系统地研究了一系列新的手性双官能膦酰胺。在温和的条件下，获得的相应氮杂-MBH加合物收率良好（75–99％），对映体过量非常好（51–95％ee）。
• Eco-friendly and efficient catalyst-free synthesis of <i>N</i>-sulfonylimines from sulfonamides and aldehydes: crucial role of Al₂O₃ as a reusable dehydrating agent
  作者：Zaineb Litim、Hanen Slimi、Thierry Ollevier、Jamil Kraïem

  DOI：10.1039/d2ra08304c

  日期：——

  A green synthesis of N-sulfonylimines was developed involving the straightforward condensation of sulfonamides with aldehydes under green and catalyst-free conditions, mediated by neutral Al₂O₃ as an efficient and reusable dehydrating agent.

  开发了一种绿色合成N-磺酰亚胺的方法，该方法涉及在无催化剂的条件下，通过中性Al2O3作为高效和可重复使用的脱水剂，直接将磺酰胺与醛缩合。
• Highly Efficient aza-Baylis−Hillman Reaction of <i>N</i>-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds
  作者：Yong-Mei Xu、Min Shi

  DOI：10.1021/jo035103p

  日期：2004.1.1

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.