1-phenyl-2-(phenylsulfonyl)ethan-1-one oxime | 908814-02-8

• 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: 1-phenyl-2-(phenylsulfonyl)ethan-1-one oxime
• 英文别名: N-[2-(benzenesulfonyl)-1-phenylethylidene]hydroxylamine
• CAS: 908814-02-8
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: WVUQXZSJMSIFGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-氟苯磺酰胺 在 2,2'-联吡啶 、 锰 、 水 、 sodium hydroxide 、 nickel dichloride 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 16.5h， 生成 1-phenyl-2-(phenylsulfonyl)ethan-1-one oxime
  参考文献：
  名称：

  Difluoroaminosulfonylation of Styrenes with N,N-Difluorobenzenesulfonamide

  摘要：

  DOI：

  10.1016/j.jfluchem.2021.109823

文献信息

• Copper-Mediated 1,2-Difunctionalization of Styrenes with Sodium Arylsulfinates and<i>tert</i>-Butyl Nitrite: Facile Access to α-Sulfonylethanone Oximes
  作者：Ji Yang、Yan-Yun Liu、Ren-Jie Song、Zhi-Hong Peng、Jin-Heng Li

  DOI：10.1002/adsc.201600109

  日期：2016.7.14

  A new copper‐mediated synthesis of α‐sulfonylethanone oximes from styrenes, sodium arylsulfinates and tert‐butyl nitrite (t‐BuONO; TBN) is presented. This intermolecular three‐component method enables the one‐step formation of CN and CS bonds under mild conditions, and represents a new, straightforward approach to α‐sulfonylethanone oximes.

  提出了一种新的由铜介导的由苯乙烯，芳基亚磺酸钠和亚硝酸叔丁酯（t- BuONO； TBN）合成的α-磺基丙酮酮肟。这种分子间三组分方法可在温和条件下一步一步形成CN和CS键，并且代表了一种新的直接方法来处理α-磺酰lethanone肟。
• TBN-mediated regio- and stereoselective sulfonylation &amp; oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H₂O
  作者：Bin Wang、Zicong Yan、Liyan Liu、Jiawei Wang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1039/c8gc02708k

  日期：——

  A difunctionalization of alkynes cascade reaction was developed to generate α-sulfonylethanone oximes in environmentally benign EtOH/H₂O.

  炔烃的双官能团化级联反应被开发出来，在环境友好的EtOH/H₂O中生成α-磺酰乙酮肟。
• Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: Novel celecoxib analogs as potent anti-inflammatory agents
  作者：Hatem A. Abdel-Aziz、Khalid A. Al-Rashood、Kamal Eldin H. ElTahir、Ghada M. Suddek

  DOI：10.1016/j.ejmech.2014.04.065

  日期：2014.6

  The reaction of arylsulfones 11a-d with hydrazonoyl chloride derivative 13 furnished celecoxib analogs 4-(3-acetyl-5-aryl-4-(arylsulfonyl)-1H-pyrazol-1-yl)benzenesulfonamides 15a-d, respectively. Oximes 16a, b and hydrazones 17a, b were prepared by reacting sulfones 11a, b with hydroxyl amine and phenyl hydrazine, respectively. The anti-inflammatory activity of the synthesized compounds showed that, 5-(4-bromophenyl)-4-(phenylsulfonyl)pyrazole 15c and 5-(4-bromophenyl)-4-(4-tolylsulfonyl)pyrazole 15d exhibited excellent anti-inflammatory activity with ED50 = 68 ± 2.2 and 51 ± 0.7 μM/kg, respectively, higher than that of celecoxib (ED50 = 86 ± 1.1 μM/kg) after 3 h with acceptable ulcer index. In addition, the LD50 of 15c and 15d is 7.1 mM/kg for each, and 9.8 mM/kg for celecoxib. Compound 15d appeared selectivity index (COX-2/COX-1) almost the half of celecoxib while 15c is non-selective for COX-2. Compound 15c with ED50 = 80 ± 2.8 μM/kg showed a significant analgesic activity when compared with celecoxib (ED50 = 70 ± 3.9 μM/kg) after 2 h whereas 15b (ED50 = 50 ± 1.2 μM/kg) and 15d (ED50 = 69 ± 2.7 μM/kg) seemed to be more potent than celecoxib (ED50 = 156 ± 4.8 μM/kg) but with a shorter duration (0.5 h).
• Difluoroaminosulfonylation of Styrenes with N,N-Difluorobenzenesulfonamide
  作者：Wenqing Zhang、Xianjin Yang

  DOI：10.1016/j.jfluchem.2021.109823

  日期：2021.8