4-(2-((4-nitrophenyl)sulfonyl)acetyl)benzonitrile | 1313054-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-((4-nitrophenyl)sulfonyl)acetyl)benzonitrile
• 英文别名: 4-[2-(4-nitrophenylsulfonyl)acetyl]benzonitrile；4-[2-(4-Nitrophenyl)sulfonylacetyl]benzonitrile
• CAS: 1313054-95-3
• 化学式: C₁₅H₁₀N₂O₅S
• 分子量: 330.321
• InChiKey: SQGJMCDSQNIANQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 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：
  129
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-甲基-3-苯基-1-丙烯 、 4-(2-((4-nitrophenyl)sulfonyl)acetyl)benzonitrile 在 copper diacetate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 反应 0.75h， 以41%的产率得到4-[5-benzyl-5-methyl-3-(4-nitrophenylsulfonyl)-4,5-dihydrofuran-2-yl]benzonitrile
  参考文献：
  名称：

  Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds

  摘要：

  A new series of monoamidoxime derivatives was synthesized using manganese(III) acetate by microwave irradiation. Several amidoximes (27-31, 33, 38) showed valuable in vitro activities toward Leishmania donovani promastigotes, exhibiting IC50 values between 5.21 and 7.89 mu M. In parallel, the cytotoxicity of these compounds was evaluated on murine J774A.1 cells, revealing the corresponding selectivity index (SI). Among the 13 tested compounds, 4 monoamidoximes (27-30) exhibited an SI more than 20 times better than pentamidine. Moreover, monoamidoxime 28 (4-[5-Benzyl-3-(4-fluorophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]-N'-hydroxybenzimidamide) is 40 times more selective than pentamidine, and 1.6 times more than amphotericin B, used as reference drug compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.026
• 作为产物：
  描述：

  4-氰基苯乙烯 、 对硝基苯磺酰氯 在 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以78%的产率得到4-(2-((4-nitrophenyl)sulfonyl)acetyl)benzonitrile
  参考文献：
  名称：

  在有氧条件下用磺酰氯在可见光下促进烯烃的氧化双官能化，从而获得β-酮砜

  摘要：

  通过可见光促进的反应，已经开发出一种温和，实用和有效的制备β-酮砜的策略。该反应涉及在温和的条件下，Ir（ppy）2（dtbbpy）PF 6催化的烯烃与磺酰氯的直接官能化反应。空气被用作氧化剂，没有任何添加剂。该转化以中等至高产率提供了相应的产物。

  DOI：

  10.1016/j.tetlet.2017.08.013

文献信息

• Functionalization of Alkynes and Alkenes Using a Cascade Reaction Approach: Synthesis of β-Keto Sulfones under Metal-free Conditions
  作者：Mukesh Kumar、Riyaz Ahmed、Maninder Singh、Shweta Sharma、Thanusha Thatikonda、Parvinder Pal Singh

  DOI：10.1021/acs.joc.9b02779

  日期：2020.1.17

  reporting a multicomponent cascade reaction approach for the synthesis of β-keto sulfones by exploiting differential reactivity pattern of substrates under open-atmosphere and metal-free conditions. The coupling partners are aryldiazonium salts, unsaturated compounds, and DABSO. The optimized conditions worked well with both alkenes and alkynes. Moreover, the reaction also works with metabisulfite for

  在这里，我们正在报道一种在开放气氛和无金属条件下通过利用底物的不同反应模式来合成β-酮砜的多组分级联反应方法。偶联伙伴是芳基重氮盐，不饱和化合物和DABSO。优化的条件对烯烃和炔烃都适用。此外，该反应还与焦亚硫酸盐一起用作砜的来源。受控液相色谱-质谱法和18 O标记的实验表明，空气是β-酮砜的酮基上引入的氧原子的来源。
• Visible-light-induced direct oxysulfonylation of alkynes with sulfonyl chlorides and HCl
  作者：Tengfei Niu、Dingyun Jiang、Bangqing Ni

  DOI：10.1016/j.tetlet.2017.09.083

  日期：2017.11

  efficient strategy to prepare β-keto sulfones has been developed by visible-light-induced reactions. This reaction involved Ir(dtbbpy)(ppy)2PF6-catalyzed direct functionalization of alkynes with sulfonyl chloride and HCl using air as the oxidant. HCl not only acted as a hydrogen source in the proton transfer process, but also played a vital role in the reaction process.

  通过可见光诱导的反应，已经开发出一种温和，实用，有效的制备β-酮砜的策略。该反应涉及Ir（dtbbpy）（ppy）2 PF 6催化的炔烃用磺酰氯和HCl的直接作用，以空气为氧化剂。HCl不仅在质子转移过程中充当氢源，而且在反应过程中也起着至关重要的作用。
• Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds
  作者：Lucie Paloque、Ahlem Bouhlel、Christophe Curti、Aurélien Dumètre、Pierre Verhaeghe、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2011.04.026

  日期：2011.7

  A new series of monoamidoxime derivatives was synthesized using manganese(III) acetate by microwave irradiation. Several amidoximes (27-31, 33, 38) showed valuable in vitro activities toward Leishmania donovani promastigotes, exhibiting IC50 values between 5.21 and 7.89 mu M. In parallel, the cytotoxicity of these compounds was evaluated on murine J774A.1 cells, revealing the corresponding selectivity index (SI). Among the 13 tested compounds, 4 monoamidoximes (27-30) exhibited an SI more than 20 times better than pentamidine. Moreover, monoamidoxime 28 (4-[5-Benzyl-3-(4-fluorophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]-N'-hydroxybenzimidamide) is 40 times more selective than pentamidine, and 1.6 times more than amphotericin B, used as reference drug compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Visible-light-promoted oxidative difunctionalization of alkenes with sulfonyl chlorides to access β-keto sulfones under aerobic conditions
  作者：Teng-fei Niu、Jing Cheng、Chang-li Zhuo、Ding-yun Jiang、Xing-ge Shu、Bang-qing Ni

  DOI：10.1016/j.tetlet.2017.08.013

  日期：2017.9

  A mild, practical and efficient strategy to prepare β-keto sulfones has been developed by visible light promoted reactions. This reaction involves Ir(ppy)2(dtbbpy)PF6 catalyzed direct funcationalization of alkenes with sulfonyl chlorides under mild conditions. Air was used as oxidant without any additives. The transformation affords the corresponding products in moderate to high yields.

  通过可见光促进的反应，已经开发出一种温和，实用和有效的制备β-酮砜的策略。该反应涉及在温和的条件下，Ir（ppy）2（dtbbpy）PF 6催化的烯烃与磺酰氯的直接官能化反应。空气被用作氧化剂，没有任何添加剂。该转化以中等至高产率提供了相应的产物。