4-phenyl-5,6-dihydro-2H-thiopyran | 73813-60-2

• 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: 4-phenyl-5,6-dihydro-2H-thiopyran
• 英文别名: 4-phenyl-3,6-dihydro-2H-thiopyran
• CAS: 73813-60-2
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: NKVCXNXOSKEWLU-UHFFFAOYSA-N

物化性质

• 熔点：
  49.5-50.5 °C
• 沸点：
  294.1±40.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4-phenyl-5,6-dihydro-2H-thiopyran 在 sodium periodate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 水 为溶剂， 反应 9.33h， 生成 2-(α-hydroxybenzyl)-4-phenyl-5,6-dihydro-2H-thiopyran 1-oxide
  参考文献：
  名称：

  Crumbie, Robyn L.; Ridley, Damon D.; Steel, Peter J., Australian Journal of Chemistry, 1985, vol. 38, # 1, p. 119 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基-四氢-2H-吡喃4-酮 在 硫酸 、 乙酸酐 作用下， 生成 4-phenyl-5,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  218.硫杂的一些反应环己-4-酮和1-烷基-4-哌啶酮

  摘要：

  DOI：

  10.1039/jr9500001059

文献信息

• Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade
  作者：Fang Li、David Calabrese、Matthew Brichacek、Ivy Lin、Jon T. Njardarson

  DOI：10.1002/anie.201108261

  日期：2012.2.20

  The fifth element: An efficient new synthetic method for accessing 3,6‐dihydro‐2H‐thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates

  第五要素：开发了一种有效的新型合成方法，可在一锅中获得3,6-dihydro-2 H - thiopyrans 1。该方法采用阴离子级联，其通过将乙烯基亲核试剂加到羰基上，然后硫代磷酸酯从S到O的迁移和分子内硫醇盐的置换来触发。该范围适用于各种酮和酯底物。
• α‐Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping
  作者：Nico Seling、Masakazu Atobe、Kevin Kasten、James D. Firth、Peter B. Karadakov、Frederick W. Goldberg、Peter O'Brien

  DOI：10.1002/anie.202314423

  日期：2024.1.8

  Lithiation and trapping at convenient temperatures (0/−10 °C) of five cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyrans and a thiomorpholine enables straightforward α-functionalisation. Trapping with a wide range of electrophiles generates more than 50 diverse α-substituted saturated sulfur heterocycles that are not easily synthesised by the currently available methods. TMEDA=N,N,N′

  五种环状硫化物（例如四氢噻吩、四氢噻喃和硫代吗啉）在方便的温度（0/−10 °C）下进行锂化和捕获，可实现直接的 α 官能化。用多种亲电子试剂捕获会产生 50 多种不同的 α-取代饱和硫杂环，这些杂环不易通过当前可用的方法合成。 TMEDA= N,N,N′,N′-四甲基乙二胺
• Chelation Assistance in the Activation of Csp3-S Bonds in Nickel-Catalyzed Cross-Coupling Reactions
  作者：Ken-Tsung Wong、Tien-Min Yuan、Maw Cherng Wang、Hsiao-Hsian Tung、Tien-Yau Luh

  DOI：10.1021/ja00099a009

  日期：1994.10

  An unprecedented chelation approach to activate C(sp)3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic carbon-sulfur bonds. When two dithioacetal functionalities are located in close proximity, selective olefination of one of these two dithioacetal groups can thus be achieved conveniently. Depending on the relative positions of the newly formed double bond and the remaining dithioacetal group, tandem olefination occurs to give the corresponding 1,5-bis-silyl-substituted pentadienes. Various neighboring heteroatom substituents (OR, OH, NR(2) as well as SR groups) can facilitate the olefination of a dithioacetal group. Poly(thioether) linkage afforded the corresponding degradation products via a B-sulfur elimination process. 1,3-Dimercapto- and 1,3-dithiolatopropanes furnish the cyclopropane formation under nickel-catalyzed reaction conditions. The reaction of a dihydrothiopyran with MeMgI in the presence of the nickel catalyst proceeds via a sulfur-coordinated ir-allyl complex, which can further activate the CS bond to give vinylcyclopropane.
• Mychajlyszyn; Jilek, Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 793,797
  作者：Mychajlyszyn、Jilek

  DOI：——

  日期：——
• CRUMBIE, R. L.;RIDLEY, D. D.;STEEL, P. J., AUSTRAL. J. CHEM., 1985, 38, N 1, 119-132
  作者：CRUMBIE, R. L.、RIDLEY, D. D.、STEEL, P. J.

  DOI：——

  日期：——