1-(4-(methylthio)phenyl)-2-phenylethane-1,2-dione | 58022-58-5

• 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-phenylethane-1,2-dione
• 英文别名: 1-(4-Methylsulfanylphenyl)-2-phenylethane-1,2-dione
• CAS: 58022-58-5
• 化学式: C₁₅H₁₂O₂S
• 分子量: 256.325
• InChiKey: PEQHNBAATLMGFG-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C(Solv: methanol (67-56-1))
• 沸点：
  421.1±28.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 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：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(methylthio)phenyl)-2-phenylethane-1,2-dione 在 ammonium acetate 、 双氧水 、 溶剂黄146 作用下， 生成 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole
  参考文献：
  名称：

  抗炎4,5-二芳基咪唑类作为选择性环氧合酶抑制剂。

  摘要：

  描述了一系列4,5-二芳基咪唑类似物的合成和活性。一种类似物的IC50为80 nM，对COX-1具有6750选择性，并在小鼠气袋模型中显示出体内效力。

  DOI：

  10.1016/s0960-894x(98)00627-1
• 作为产物：
  描述：

  茴香硫醚 在 三氯化铝 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 1-(4-(methylthio)phenyl)-2-phenylethane-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

文献信息

• 1,2-二羰基类化合物及其合成方法
  申请人：华东师范大学

  公开号：CN110183341A

  公开（公告）日：2019-08-30

  本发明公开了一种1，2‑二羰基类化合物(1，2‑二羰基酰胺或α‑二酮类化合物)的合成方法，以1，2‑二羰基硫酯类化合物作为1，2‑二羰基试剂，在适当条件下，与胺类化合物或者硼酸酐类化合物反应，分别可以合成一系列1，2‑二羰基类化合物。本发明利用稳定的1，2‑二羰基硫酯类化合物作为二羰基化试剂，在温和条件下，一步构建得到1，2‑二羰基类化合物，避免了传统使用不稳定的α‑羰基酰氯合成1‑2二羰基化合物的弊端。
• Benzenesulfonamide subtituted imidazolyl compounds for the treatment of
  申请人：——

  公开号：US05620999A1

  公开（公告）日：1997-04-15

  A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from lower alkyl, lower haloalkyl, lower hydroxyalkyl, lower aralkenyl, lower aryloxyalkyl, lower arylthioalkyl and heteroaryl; wherein R.sup.3 is selected from lower alkyl and amino; and wherein R.sup.4 is one or more radicals selected from hydrido, halo, lower alkyl and lower alkoxy; or where R.sup.4 together with the phenyl radical forms naphthyl or benzodioxolyl; provided R.sup.1 is not lower alkyl when R.sup.3 is methyl and when R.sup.4 is hydrido, methyl, methoxy or chloro; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由式II定义，其中R.sup.1从较低的烷基、较低的卤代烷基、较低的羟基烷基、较低的芳基烯基、较低的芳氧基烷基、较低的芳硫基烷基和杂芳基中选择；其中R.sup.3从较低的烷基和氨基中选择；其中R.sup.4是从氢化物、卤素、较低的烷基和较低的烷氧基中选择的一个或多个基团；或者R.sup.4与苯基一起形成萘基或苯二氧杂基；在R.sup.3为甲基且R.sup.4为氢化物、甲基、甲氧基或氯时，提供R.sup.1不是较低烷基；或其药用盐。
• Room-Temperature Ionic Liquid–DMSO Promoted and Improved One-Pot Synthesis of 5,6-Diaryl-1,2,4-triazines
  作者：Riyaj S. Tamboli、Rajani Giridhar、Hemant M. Mande、Shailesh R. Shah、Mange Ram Yadav

  DOI：10.1080/00397911.2014.891040

  日期：2014.8.3

  improved and rapid one-pot synthesis of 5,6-diarylsubstituted-1,2,4-triazines in a mixture of room-temperature ionic liquid 1,3-dibutylimidazolium bromide [Bbim]+Br− and dimethylsulfoxide (DMSO) is described without the need for any added catalyst. Different polar aprotic solvents were screened along with ionic liquids and a synergistic effect with DMSO has been found. The predominance of one regioisomer

  摘要 在室温离子液体溴化 1,3-二丁基咪唑鎓 [Bbim]+Br− 和二甲亚砜 (DMSO) 的混合物中改进和快速一锅法合成 5,6-二芳基取代的-1,2,4-三嗪是无需任何添加的催化剂进行描述。与离子液体一起筛选了不同的极性非质子溶剂，并发现了与 DMSO 的协同效应。还研究了在不同反应温度下一种区域异构体优于另一种区域异构体的情况。通过简单的后处理程序实现了在短时间内获得出色分离产量的一锅法。离子液体被有效回收并重复使用3次而没有失去催化作用。所有化合物均通过红外、核磁共振、质谱和元素分析进行​​表征。图形概要
• Selective Metal-Free Deoxygenation of Unsymmetrical 1,2-Dicarbonyl Compounds by Chlorotrimethylsilane and Sodium Iodide
  作者：Ling-Zhi Yuan、Dolor Renko、Ilhem Khelifi、Olivier Provot、Jean-Daniel Brion、Abdallah Hamze、Mouad Alami

  DOI：10.1021/acs.orglett.6b01491

  日期：2016.7.1

  For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yields and with a total α-regioselectivity at room temperature. Identification of benzoin intermediates is achieved, and a mechanistic radical process

  首次将氯三甲基硅烷与NaI的组合用作对1,2-二酮的选择性还原体系。用几种不对称的苯甲腈衍生物成功评估了这种组合，这些衍生物以良好的收率降低，在室温下具有总的α-区域选择性。实现了对安息香中间体的鉴定，并提出了机理自由基过程。
• Synthesis, antileukemic and antiplatelet activities of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines
  作者：R. Ramajayam、Rajani Giridhar、M.R. Yadav、R. Balaraman、Hakim Djaballah、David Shum、Constantin Radu

  DOI：10.1016/j.ejmech.2007.11.023

  日期：2008.9

  The synthesis, antileukemic and antiplatelet activity evaluation of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines are described. In general, it was found that compound 17o showed moderate antileukemic activity against MOLT3 human leukemic cancer cell lines. An arachidonic acid induced platelet aggregation effect on washed rat platelets was studied. Compound 17i was found to be the most potent. The antiplatelet

  描述了2,3-二芳基-6,7-二氢-5H-1,4-二氮杂卓的合成，抗白血病和抗血小板活性的评价。通常，发现化合物17o显示出对MOLT3人白血病癌细胞系的中等抗白血病活性。研究了花生四烯酸对洗涤过的大鼠血小板的血小板聚集作用。发现化合物17i是最有效的。抗血小板特性可以通过干扰花生四烯酸途径来介导。