2,4,6-triphenyl-4H-thiopyran | 7584-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 2,4,6-triphenyl-4H-thiopyran
• CAS: 7584-36-3
• 化学式: C₂₃H₁₈S
• 分子量: 326.462
• InChiKey: POJUGLCYFXHQPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-triphenyl-4H-thiopyran 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 0.67h， 以37%的产率得到2-benzoyl-3,5-diphenylthiophene
  参考文献：
  名称：

  Drevko, B. I.; Smushkin, M. I.; Kharchenko, V. G., Russian Journal of Organic Chemistry, 1995, vol. 31, # 9, p. 1298 - 1299

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-Tri-phenylthiapyrylium tetrafluoroborate 生成 2,4,6-triphenyl-4H-thiopyran
  参考文献：
  名称：

  XARCHENKO, V. G.;BOZHENOVA, O. A.;SHEBALDOVA, A. D., ZH. ORGAN. XIMII, 1982, 18, N 11, 2435-2439

  摘要：

  DOI：

文献信息

• Substituent effects in reductions of heteroaromatic cations
  作者：David Heyes、Ramesh S. Menon、C. Ian. F. Watt、Jake Wiseman、Przemyslaw Kubinski

  DOI：10.1002/poc.532

  日期：2002.10

  structural features in the cations, radicals and anions in each series. Rates and products were determined for reductions of the pyrylium and thiopyrylium cations by sodium cyanoborohydride and of all cations by sodium borohydride in acetonitrile solution. Reactions are first order in reducing agent and cation. Primary kinetic isotope effects were determined for borohydride reduction of the least reactive

  制备一组在苯环中带有一系列取代基的2,4,6-三苯基吡啶鎓，-硫代吡啶鎓和-N-甲基吡啶鎓四氟硼酸酯中的每一个。确定了第一和第二波降低电位。对于thiopyrylium系列，标度势（E°/ 0.05915）和苯基侧基中取代基的哈米特常数总和（第一波和第二波分别为2.29和3.38）。对于吡咯鎓系列，对于第一波降低电势的所有取代基模式，都获得了良好的线性关系（σ= 2.79），但是对于第二波，对于4-苯基中带有取代基的盐和那些带有取代基的盐，它们具有独立的相关性。在2-和6-苯基上。对于吡啶鎓系列，对于在4-苯基中带有取代基的盐与在2-苯基和6-苯基中带有取代基的盐，第一波电势显示出独立的相关性，但是对于第二个波电势则具有单一的线性关系。这些与每个系列的阳离子，自由基和阴离子中的特定结构特征有关。确定了在乙腈溶液中氰基硼氢化钠还原吡喃鎓和硫代吡啶鎓阳离子以及所有阳离子通过硼氢化钠还原的速率和
• A novel reaction of 2,4,6-triphenyl(thio)selenopyrylium salts leading to benzoyl(thio)selenophenes and 2,4,6-triphenyl(thio)selenopyrans
  作者：B. I. Drevko、E. G. Bol’shakova、A. F. Almaeva、M. A. Suchkov、V. G. Mandych、G. A. Shekhter

  DOI：10.1007/s11172-009-0207-z

  日期：2009.7

  Thio- and selenopyrylium salts undergo simultaneous oxidation, leading to the corresponding benzoylselenophene or benzoylthiophene, and reduction reactions leading to 4H-selenopyran or 4H-thiopyran In the presence of water and triethylamine.

  硫代-和硒代吡喃盐同时进行氧化，产生相应的苯甲酰硒吩或苯甲酰噻吩，并在水和三乙胺存在下发生还原反应，产生 4H-硒吡喃或 4H-噻喃。
• Efficient Reduction of Thiopyrylium Salts to Corresponding 2H- and 4H-Thiopyrans Under Solvent-Free Condition: Regioselectivity and Mechanism
  作者：Arash Mouradzadegun、Nargess Gheitasvand

  DOI：10.1080/10426500590912682

  日期：2005.3.2

  Abstract A solvent-free reduction of 2,4,6-triarylthiopyrylium with NaBH4/alumina is described. The regioselectivity of these reductions were compared with those obtained in solution experiments.

  摘要 描述了用 NaBH4/氧化铝无溶剂还原 2,4,6-三芳基硫代吡喃鎓。这些还原的区域选择性与在溶液实验中获得的那些进行了比较。
• Beddoes, Roy; Heyes, David; Menon, Ramesh S., Journal of the Chemical Society. Perkin transactions II, 1996, # 3, p. 307 - 320
  作者：Beddoes, Roy、Heyes, David、Menon, Ramesh S.、Watt, C. Ian. F.

  DOI：——

  日期：——
• Improved intermolecular hydride transfer using task-specific ionic liquid: a reasonable and environmentally benign approach for the synthesis of bioactive 2H-thiopyran derivatives
  作者：Arash Mouradzadegun、Zeynab Najafi、Somayeh Elahi

  DOI：10.1080/17415993.2015.1077388

  日期：2015.11.2

  The present study describes, for the first time, the application of 1-n-butyl-3-methylimidazolium borohydride ([bmim]BH4) as task-specific ionic liquid for highly regioselective reduction of triarylthiopyrylium salts. This method furnished a straightforward route for the synthesis of valuable 2H-thiopyrans derivatives, which are widely present as motifs in an assortment of biologically active molecules, in satisfactory yields, and excellent conversions without any conventional catalyst and organic solvent.[GRAPHICS].