trans-2,6-Diphenyltetrahydrothiopyran-4-one | 18456-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: trans-2,6-Diphenyltetrahydrothiopyran-4-one
• 英文别名: (±)-trans-2,6-diphenyltetrahydrothiopyran-4-one；trans-2,3,5,6-Tetrahydro-2,6-diphenylthiopyran-4-one；trans-2,6-diphenyl-2,3,5,6-tetrahydrothiapyran-4-one；trans-2,6-diphenyltetrahydro-4H-thiopyran-4-one；trans-2,6-Diphenyltetrahydrothiapyran-4-one；r-2,trans-6-diphenyl-4-thianone；(2S,6S)-2,6-diphenylthian-4-one
• CAS: 18456-45-6
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: PPJHHCQGZVIWAR-IRXDYDNUSA-N

物化性质

• 沸点：
  447.7±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  trans-2,6-Diphenyltetrahydrothiopyran-4-one 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 240.0h， 以70%的产率得到trans-2,3,5,6-Tetrahydro-2,6-diphenylthiopyran-4-one 1,1-dioxide
  参考文献：
  名称：

  Oxygen-17 nuclear magnetic resonance spectroscopy of organosulfur compounds. 2. 17O NMR lanthanide-induced shifts (LIS) of diastereotopic sulfonyl oxygens in substituted six-membered-ring sulfones

  摘要：

  The O-17 NMR shifts of diastereotopic sulfonyl oxygens within a series of conformationally homogeneous six-membered-ring organosulfur compounds have been determined. Their lanthanide-induced shifts (LIS), resulting from competitive complexation with the europium metal ion (i.e., Eu(fod)3), provide structural insights into the relative binding potential of the attached diastereotopic sulfonyl oxygens.

  DOI：

  10.1021/jo00019a023
• 作为产物：
  描述：

  苯甲醛 在 硫化氢 、 sodium acetate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 trans-2,6-Diphenyltetrahydrothiopyran-4-one
  参考文献：
  名称：

  Spectral characterization and crystal structure of some 2,6-diarylthian-4-one hydrazone derivatives

  摘要：

  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.

  DOI：

  10.1016/j.molstruc.2014.07.080

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。
• Reactivities of variously substituted 4-heteracyclohexanones in the formation of oximes
  作者：Kuppusamy Selvaraj、Palaniappan Nanjappan、Kondareddiar Ramalingam、Krishnasamy Ramarajan

  DOI：10.1039/p29830000049

  日期：——

  The rates of oxime formation of 41 heterocyclic ketones have been measured at 5 °C in aqueous alcoholic solution buffered at pH 6.85. The data indicate an overall second-order reaction, first order each in ketone and hydroxylamine. In all cases investigated the reaction appears to be irreversible under the experimental conditions employed. Increased steric retardation is observed as steric crowding

  已在5°C的pH值为6.85的酒精水溶液中测定了41种杂环酮的肟形成速率。数据表明总体为二级反应，一级反应分别为酮和羟胺。在所研究的所有情况下，该反应在所采用的实验条件下似乎都是不可逆的。随着在羰基官能团周围的空间拥挤的增加，观察到增加的空间延迟，这表明发生了确定胺基对羰基基团的速率的攻击。4-哌啶酮，oxan-4-ones，thian-4-ones，相应的1,1-dioxides和selenan-4-ones肟的形成速率有显着差异。
• Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane
  作者：N. Geoffrey Rule、Michael R. Detty、Jeanne E. Kaeding、John A. Sinicropi

  DOI：10.1021/jo00111a027

  日期：1995.3

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.
• 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.
• Arndt; Nachtwey; Pusch, Chemische Berichte, 1925, vol. 58, p. 1641
  作者：Arndt、Nachtwey、Pusch

  DOI：——

  日期：——