cis-2,6-di(p-tolyl)tetrahydrothiopyran-4-one | 69788-07-4

• 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: cis-2,6-di(p-tolyl)tetrahydrothiopyran-4-one
• 英文别名: trans-2,6-Di-p-tolyltetrahydrothiopyran-4-on；(2R,6S)-2,6-bis(4-methylphenyl)thian-4-one
• CAS: 69788-07-4
• 化学式: C₁₉H₂₀OS
• 分子量: 296.433
• InChiKey: NMQIKCBARJZWSJ-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2,6-di(p-tolyl)tetrahydrothiopyran-4-one 、 苄氧基胺盐酸盐 在 sodium acetate trihydrate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以92%的产率得到r-2,c-6-bis(p-methylphenyl)tetrahydrothiopyran-4-one O-benzyloxime
  参考文献：
  名称：

  Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles

  摘要：

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.038
• 作为产物：
  描述：

  bis(4-methylstyryl)ketone 在 硫化氢 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 cis-2,6-di(p-tolyl)tetrahydrothiopyran-4-one
  参考文献：
  名称：

  Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles

  摘要：

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.038

文献信息

• Diastereoselective Synthesis of 2,6-Diaryltetrahydrothiopyran-4-ones by Phase-Transfer Catalysis
  作者：Thibault Gendron、Hripsimée Kessedjian、Elisabeth Davioud-Charvet、Don Antoine Lanfranchi

  DOI：10.1002/ejoc.201403516

  日期：2015.3

  Two efficient phase-transfer-catalyzed protocols for the diastereoselective synthesis of cis and trans isomers of 2,6-diaryltetrahydrothiopyran-4-ones (2,6-DATHTPs) have been developed. In a study of the scope of the reactions, differently substituted 2,6-DATHTPs were successfully accessed in high yields and diastereomeric excessses on both experimental and preparative scales.

  已经开发了两种有效的相转移催化方案，用于非对映选择性合成 2,6-二芳基四氢噻喃-4-酮 (2,6-DATHTPs) 的顺式和反式异构体。在对反应范围的研究中，不同取代的 2,6-DATHTP 在实验和制备规模上均以高产率和非对映体过量成功获得。
• US9174960B2
  申请人：——

  公开号：US9174960B2

  公开（公告）日：2015-11-03
• Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
  作者：Paramasivam Parthiban、Gopalakrishnan Aridoss、Paramasivam Rathika、Venkatachalam Ramkumar、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2009.04.038

  日期：2009.6

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Spectral characterization and crystal structure of some 2,6-diarylthian-4-one hydrazone derivatives
  作者：C. Sankar、S. Umamatheswari、K. Pandiarajan

  DOI：10.1016/j.molstruc.2014.07.080

  日期：2014.11

  A series of cis and trans 2,6-diarylthian-4-one hydrazone derivatives (11-16) have been synthesized and characterized by H-1, C-13 and two dimensional NMR spectroscopy. For the 2r,6t-diphenylthian-4-one N-isonicotinoylhydrazone (14) X-ray diffraction have also been recorded. The coupling constants suggested that the cis-hydrazones (11-13), which have the phenyl groups in cis orientation, largely exist in chair conformations with equatorial orientation of the phenyl groups 11C. Analysis of the vicinal coupling constants of trans-hydrazones (14-16) suggests that boat forms 14B must make significant contributions to it and the relative population is 58%. Moreover, in solution chair conformations 14C and 14C', may contribute to 14. The NOESY and X-ray diffraction of 14 gives definite evidence for the contribution of 14C. (C) 2014 Elsevier B.V. All rights reserved.