1-[4-(methylthio)phenyl]-2-(4-nitrophneyl)ethanone | 440121-13-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-[4-(methylthio)phenyl]-2-(4-nitrophneyl)ethanone
• 英文别名: 4-methylsulfanyl-4'-nitro-deoxybenzoin；4-Methylmercapto-4'-nitro-desoxybenzoin；1-(4-Methylsulfanylphenyl)-2-(4-nitrophenyl)ethanone
• CAS: 440121-13-1
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: CZRKWDYWNCBHMX-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  484.3±30.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-(methylthio)phenyl]-2-(4-nitrophneyl)ethanone 在 selenium(IV) oxide 、 双氧水 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 生成 1-(4-Methanesulfonyl-phenyl)-2-(4-nitro-phenyl)-ethane-1,2-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033
• 作为产物：
  描述：

  对硝基苯乙酸 在 三氯化铝 、 三氯化磷 作用下， 生成 1-[4-(methylthio)phenyl]-2-(4-nitrophneyl)ethanone
  参考文献：
  名称：

  Shirude; Patel; Giridhar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1080 - 1085

  摘要：

  DOI：

文献信息

• Simple and Efficient Procedure for the Friedel–Crafts Acylation of Aromatic Compounds with Carboxylic Acids in the Presence of P₂O₅/AL₂O₃Under Heterogeneous Conditions
  作者：Abdol R. Hajipour、Amin Zarei、Leila Khazdooz、Arnold E. Ruoho

  DOI：10.1080/00397910802663436

  日期：2009.7.7

  Abstract An efficient and chemoselective method for the Friedel–Crafts acylation of aromatic compounds using P2O5/Al2O3 and carboxylic acids. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones in good yields.

  摘要 一种使用 P2O5/Al2O3 和羧酸对芳香族化合物进行 Friedel-Crafts 酰化的高效化学选择性方法。芳香族和脂肪族羧酸都容易反应，以良好的产率得到相应的芳香酮。
• Friedel–Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions
  作者：Amin Zarei、Abdol R. Hajipour、Leila Khazdooz

  DOI：10.1016/j.tetlet.2008.09.062

  日期：2008.11

  A convenient and efficient procedure for the Friedel–Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 is described. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages

  描述了一种在P 2 O 5 / SiO 2存在下芳族化合物与羧酸的Friedel-Crafts酰化的简便有效的方法。芳族和脂族羧酸都容易反应，得到相应的芳族酮。该方法的优点是使用无毒且廉价的材料，简单且清洁的后处理，较短的反应时间和良好的产物收率。
• Estrogenic Thio-Analogs of the Dimethyl Ethers of Diethylstilbestrol, its Homologs, and Hexestrol
  作者：Michinori Oki

  DOI：10.1246/bcsj.25.112

  日期：1952.2
• A Facile One-Pot Synthesis of 4,5-Diaryl-2,2-dimethyl-3(2H)-furanones
  作者：Ki-Wha Lee、Young Hoon Choi、Yung Hyup Joo、Jin Kwan Kim、Song Seok Shin、Young Joo Byun、Yeonjoon Kim、Shin Chung

  DOI：10.1016/s0968-0896(01)00388-1

  日期：2002.4

  An efficient and practical one-pot synthesis of 4,5-diaryl-2,2-dimethyl-3(2H)-furanones has been achieved from 1,2-diarylethanones and 2-bromoisobutyryl cyanide in the presence of excess base. by employing the 'hard soft acid base' principle. The reaction scope of 2-bromoisobutyryl cyanide could be expanded to prepare a variety of 2,2-dimethyl-3(2H)-furanone derivatives other than 4,5-diaryl-2,2-dimethyl-3(2H)-furanones. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors
  作者：Sunil K. Singh、V. Saibaba、V. Ravikumar、Santosh V. Rudrawar、Pankaj Daga、C.Seshagiri Rao、V. Akhila、P. Hegde、Y.Koteswar Rao

  DOI：10.1016/j.bmc.2004.01.033

  日期：2004.4

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.