trans-2,3,5,6-Tetrahydro-2,6-diphenylthiopyran-4-one 1,1-dioxide | 34379-72-1

• 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-2,3,5,6-Tetrahydro-2,6-diphenylthiopyran-4-one 1,1-dioxide
• 英文别名: trans-2,6-Diphenyltetrahydrothiopyran-4-one 1,1-Dioxide；(+/-)-1,1-dioxo-2r,6t-diphenyl-tetrahydro-1λ⁶-thiopyran-4-one；(+/-)-1,1-Dioxo-2r,6t-diphenyl-tetrahydro-1λ⁶-thiopyran-4-on；1,1-Dioxo-2,6-diphenyl-tetrahydro-1λ⁶-thiopyran-4-on；(2R,6R)-1,1-dioxo-2,6-diphenylthian-4-one
• CAS: 34379-72-1
• 化学式: C₁₇H₁₆O₃S
• 分子量: 300.378
• InChiKey: UEPWZKMHEHTBRW-IAGOWNOFSA-N

物化性质

• 沸点：
  547.8±50.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2,3,5,6-Tetrahydro-2,6-diphenylthiopyran-4-one 1,1-dioxide 在 tripropylammonium fluorochromate (VI) 作用下， 以 水 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  Pillay, M. Krishna; Kasthuri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 9, p. 738 - 744

  摘要：

  DOI：
• 作为产物：
  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

文献信息

• 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。
• Cyclic sulfones from double conjugate addition of Rongalite
  作者：Melina Goga、Hao Zong、Jazmine Prana、Rudolph Michel、Antonia Muro、Elana Rubin、Janet Brenya、Magnus W. P. Bebbington

  DOI：10.1080/00397911.2023.2222316

  日期：2023.8.18

  Abstract Cyclic sulfones are obtained in up to 92% yield by double conjugate addition of Rongalite (sodium hydroxymethyl sulfinate) to dienones. The major product in each case is the kinetic trans-isomer of the 3,5-disubstituted ketosulfone. Eleven examples, including aryl and alkyl substituted substrates, are reported. The advantages of the method are its experimental simplicity, tolerance for both

  摘要 通过将雕白粉（羟甲基亚磺酸钠）与二烯酮进行双共轭加成，可以得到环状砜，收率高达 92%。每种情况下的主要产物是3,5-二取代酮砜的动力学反式异构体。报道了十一个例子，包括芳基和烷基取代的底物。该方法的优点是实验简单、对质子和氧化敏感官能团的耐受性以及具有空间挑战性的底物。这项工作还显着扩展了雕白粉作为共轭亲核试剂的范围。
• 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.
• Arndt; Nachtwey; Pusch, Chemische Berichte, 1925, vol. 58, p. 1641
  作者：Arndt、Nachtwey、Pusch

  DOI：——

  日期：——
• Sivakumar, N.; Nagalingam, J.; Palanisamy, A. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 531 - 534
  作者：Sivakumar, N.、Nagalingam, J.、Palanisamy, A. M.、Premkumar, V.、Natarajan, K.、et al.

  DOI：——

  日期：——