3,3-双甲基磺酰基-1-(4-硝基苯基)-丙酮 | 81375-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3-双甲基磺酰基-1-(4-硝基苯基)-丙酮
• 英文名称: Bis(methylthio)-3,3-(nitro-4 phenyl)-1 propene-2 one-1
• 英文别名: 4-nitrophenyl α-oxoketen dithioacetal；1-(4-nitrophenyl)-3-bis(methylthio)propen-1-one；3,3-bis(methylthio)-1-(4-nitrophenyl)prop-2-en-1-one；3,3-Bis(methylsulfanyl)-1-(4-nitrophenyl)prop-2-en-1-one
• CAS: 81375-97-5
• 化学式: C₁₁H₁₁NO₃S₂
• 分子量: 269.345
• InChiKey: ZRMKIXVMEJWMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-双甲基磺酰基-1-(4-硝基苯基)-丙酮 在 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 反应 0.41h， 生成 2-[3,3-bis(methylsulfanyl)-2-(4-nitrobenzoyl)-2-propenylidene]malononitrile
  参考文献：
  名称：

  A Convenient Preparation of 2-Aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and Their Application in the Synthesis of 5-Aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles

  摘要：

  对芳酰基烯二硫乙酯1与由POCl3和DMF制备的Vilsmeier-Haack试剂在温和条件下反应，得到了优良产率的2-芳酰基-3,3-双(烷基硫基)丙烯醛2。由2和马来腈衍生的2-[2-芳酰基-3,3-双(甲基硫基)-2-丙烯基]马来腈3在浓盐酸和叔丁醇存在下环化，得到2-吡啶酮衍生物4。

  DOI：

  10.1055/s-2005-918491
• 作为产物：
  描述：

  3,3-二氯-1-(4-硝基苯基)丙-2-烯-1-酮 、 sodium thiomethoxide 以 乙醚 、 乙腈 为溶剂， 反应 2.0h， 以68%的产率得到3,3-双甲基磺酰基-1-(4-硝基苯基)-丙酮
  参考文献：
  名称：

  6-Alkylthio-1,3-thiazinium-salze aus Acylketen-S,S-acetalen und Thioamiden

  摘要：

  DOI：

  10.1055/s-1982-29748

文献信息

• [EN] COMPOUNDS FOR INHIBITING TNIK AND MEDICAL USES THEREOF<br/>[FR] COMPOSÉS DESTINÉS À L'INHIBITION DE TNIK ET UTILISATIONS MÉDICALES ASSOCIÉES
  申请人：KOREA RES INST CHEMICAL TECH

  公开号：WO2019156439A1

  公开（公告）日：2019-08-15

  The present disclosure provides the compound having inhibitory property against TNIK having a specific chemical structure or its pharmaceutically acceptable salt. The present disclosure also provides a composition comprising the compound or its pharmaceutically acceptable salt. The present disclosure also provides a medical use of the compound, its salt or the composition comprising the compound or its pharmaceutically acceptable salt for treating or preventing cancer. The present disclosure also provides a method of treatment or prevention of cancer comprising administering the compound, its salt or the composition comprising the compound or its salt to a subject in need of such treatment or prevention.

  本公开提供了具有抑制TNIK活性的化合物，其具有特定化学结构或其药用可接受盐。本公开还提供了包含该化合物或其药用可接受盐的组合物。本公开还提供了该化合物、其盐或包含该化合物或其药用可接受盐的组合物的医疗用途，用于治疗或预防癌症。本公开还提供了一种治疗或预防癌症的方法，包括向需要此类治疗或预防的受试者施用该化合物、其盐或包含该化合物或其盐的组合物。
• Synthesis and Molecular Docking Studies of Novel 2-(2-Amino-6-Phenyl-4-Pyrimidinylamino) Ethanol Derivatives: Using Ring-Opening Reactions of Cyclic Ketene-N,O-Acetal
  作者：Ravi Kumar G. M. V. N. A. R.、Arumugam Thangamani

  DOI：10.13005/ojc/330361

  日期：2017.6.28

  A series of six novel 2-(2-amino-6-phenyl-4-pyrimidinylamino) ethanol derivatives have been synthesized starting from commercially available substituted acetophenones via OxoketeneDithioacetals with high yields. Ketene dithioacetals to react with 2-aminoethanol or l-amino-2-propanol to afford the corresponding substituted 2-methyleneoxazolidines which are utilized in the synthesis of 6-aryl-2-amino-4-pyrimidinamine Derivatives. The molecular docking studies revealed that all the synthesized compounds best fit into the active site of HDAC2, anti-cancer protein.

  一系列新型2-(2-氨基-6-苯基-4-嘧啶基氨基)乙醇衍生物，通过商品化的取代苯乙酮与奥克烯二硫代乙缩醛的高产率反应合成。通过酮烯二硫代乙缩醛与2-氨基乙醇或L-氨基-2-丙醇反应，得到相应的取代2-亚甲基噁唑烷，进而合成6-芳基-2-氨基-4-嘧啶胺衍生物。分子对接研究揭示，所有合成化合物均能最佳地适应HDAC2抗癌蛋白的活性部位。
• Synthetic studies on KF-alumina-catalysed reaction of substituted and unsubstituted aryl-oxoketene dithioacetals and 1H-pyrazone-5(4H)-one: a convenient synthesis of pyrazolo[3,4-b]pyridine and pyrazolo[1,5-a]pyrimidine
  作者：Pushpak Mizar、Bekington Myrboh

  DOI：10.1016/j.tetlet.2009.04.020

  日期：2009.6

  The procedures described herein provide a facile method for the synthesis of pyrazolo[3,4-b]pyridine and pyrazolo[1,5-a]pyrimidine by reacting N-substituted or unsubstituted-pyrazol-5(4H)-one, aryl-oxoketene dithioacetals and alkyl amide. The products were obtained in moderate to good yield. The effects of the solvents and substitution have also been described.

  本文所述的方法提供了通过使N-取代的或未取代的吡唑-5（4H）-一个芳基反应来合成吡唑并[3,4- b ]吡啶和吡唑并[1,5- a ]嘧啶的简便方法。-氧杂环丁烯二硫缩醛和烷基酰胺。以中等至良好的产率获得产物。还描述了溶剂和取代的作用。
• Synthesis of 3-Aroylnicotinonitriles from Aroylketene Dithioacetals
  作者：C. Asokan、E. Anabha、K. Nirmala、Abraham Thomas

  DOI：10.1055/s-2006-958964

  日期：2007.2

  The Knoevenagel adducts of 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and malononitrile were cyclized in the presence of diisopropylamine to afford 5-aroyl-2,6-bis(methylsulfanyl)nicotinonitriles. Cyclization in the presence of aqueous ammonia gave 2-amino-5-aroyl-6-(methylsulfanyl) nicotinonitriles. A multicomponent reaction involving aroylketene dithioacetals, malononitrile and Vilsmeier reagent gave 5-aroyl-2-chloro-6-(methylsulfanyl)nicotinonitrile.

  2-aroyl-3,3-bis(alkylsulfanyl)acryaldehydes 和丙二腈的 Knoevenagel 加合物在二异丙基胺存在下发生环化反应，生成 5-aroyl-2,6-bis(methylsulfanyl)nicotinonitriles。在氨水存在下进行环化，可得到 2-氨基-5-芳酰基-6-(甲硫基)烟腈。在涉及芳基乙烯二硫代乙酸酯、丙二腈和 Vilsmeier 试剂的多组分反应中，生成了 5-芳酰基-2-氯-6-(甲硫基)烟腈。
• Transition metal free, green and facile halogenation of ketene dithioacetals using a KX–oxidant system
  作者：Vishakha Rai、Ganesh Shivayogappa Sorabad、Mahagundappa Rachappa Maddani

  DOI：10.1039/d0nj03737k

  日期：——

  A facile oxidative halogenation of α-oxo ketene dithioacetals is achieved by using a potassium halide and oxidant combination under transition metal free conditions at ambient temperature. Using this methodology, halogenated ketene dithioacetals are synthesized in good to excellent yields with a short reaction time. The halogenated products are successfully transformed into nitrogen containing heterocyclic

  通过在环境温度下在不含过渡金属的条件下使用卤化钾和氧化剂的组合，可实现α-氧代烯酮二硫缩醛的简便氧化卤化。使用这种方法，可以在短时间内以良好至极好的收率合成卤代乙烯酮二硫缩醛。卤化产物成功地转化为含氮杂环分子。