3,6-diphenyl-2H-pyran-2-one | 17372-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,6-diphenyl-2H-pyran-2-one
• 英文别名: 3,6-diphenyl-2-pyrone；3,6-diphenyl-pyran-2-one；3,6-Diphenyl-pyran-2-on；3,6-diphenylpyran-2-one
• CAS: 17372-49-5
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: NYBDYBUDQAUEGV-UHFFFAOYSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  479.1±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-diphenyl-2H-pyran-2-one 、 phenyl[tris(trimethylsilyl)phenyl]iodonium triflate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 以50%的产率得到2,3-bis(trimethylsilyl)-5,8-diphenylnaphthalene
  参考文献：
  名称：

  Organization of Acenes with a Cruciform Assembly Motif

  摘要：

  This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were compared with DFT-optimized geometries. Both crystallographic and computed structures show that a planar acene core is the exception rather than the rule. In the assembly of these molecules, the phenyl groups block the herringbone motif and further guide the arrangement of the acene core into higher order structures. The packing for the phenyl-substituted derivatives is dictated by close contacts between the C-H's of the pendant aromatic rings and the carbons at the fusions in the acene backbone. Using thiciphene substituents instead of phenyls creates cofacially stacked acenes. In thin films, the thiophene-substituted derivative forms devices with good electrical properties: relatively high mobility, high ON/OFF ratios, and low threshold voltage for device activation. An unusual result is obtained for the decaphenyl pentacene when devices are fabricated on its crystalline surface. Although its acene cores are well isolated from each other, this material still exhibits good electrical properties.

  DOI：

  10.1021/ja0570786
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.05h， 以78%的产率得到3,6-diphenyl-2H-pyran-2-one
  参考文献：
  名称：

  甲锡烷基化的α-吡喃酮类化合物：合成，卤化和脱甲锡反应

  摘要：

  乙炔基三丁基锡与各种1,3,4-恶二嗪-6-酮进行逆型[4 + 2]环加成反应，得到两个区域异构的甲锡烷基化的α-吡喃酮，可通过快速柱色谱分离。将锡烷暴露于氯仿或THF中作为溶剂的元素卤素中，得到相应的卤代吡喃酮。还描述了该反应类型的一般例外。用干燥的氯化氢去甲锡烷基化可提供3，6-二取代的α-吡喃酮。

  DOI：

  10.1016/s0040-4020(98)00754-6

文献信息

• Carbene Catalyzed Access to 3,6‐Disubstituted <i>α</i> ‐Pyrones via Michael Addition/Lactonization/Elimination Cascade
  作者：Anil Kumar Khatana、Vikram Singh、Manoj Kumar Gupta、Bhoopendra Tiwari

  DOI：10.1002/adsc.202100760

  日期：2021.11.9

  metal-free access to 3,6-disubstituted α-pyrones from α-chloro aldehydes and β-tosyl enones is reported. The reactions proceed via the Michael addition/lactonization/elimination cascade. The regioselective addition of NHC-bound enolates/homoenolates to the enones bearing a bulkier functionality such as tosyl group at the β-position has remained challenging. The 3,6-disubstituted α-pyrones could be converted

  报道了第一个从α-氯醛和β-甲苯磺酰基烯酮直接无过渡金属获得 3,6-二取代α-吡喃酮的方法。反应通过迈克尔加成/内酯化/消除级联进行。将 NHC 结合的烯醇化物/同烯醇化物区域选择性地添加到具有更大官能团（例如β位的甲苯磺酰基）的烯酮中仍然具有挑战性。3,6-二取代的α-吡喃酮可以通过简单的方法转化为有价值的产品，如1,2,3,4-四取代苯、1,4-二取代萘以及蒽和6,13-​​二取代二氢乙烯并五苯。手术。
• Christl, Manfred; Bodenschatz, Gabriele; Feineis, Erich, Liebigs Annalen, 1996, # 5, p. 853 - 861
  作者：Christl, Manfred、Bodenschatz, Gabriele、Feineis, Erich、Hegmann, Joachim、Huettner, Gerhard、Mertelmeyer, Stefan、Schaetzlein, Klaus

  DOI：——

  日期：——
• 2-Pyrones. XXV. 3,6-Diaryl-2-pyrones as Heterocyclic Analogs of Terphenyl
  作者：Richard H. Wiley、C. H. Jarboe、F. N. Hayes

  DOI：10.1021/ja01567a065

  日期：1957.5
• Organization of Acenes with a Cruciform Assembly Motif
  作者：Qian Miao、Xiaoliu Chi、Shengxiong Xiao、Roswitha Zeis、Michael Lefenfeld、Theo Siegrist、Michael L. Steigerwald、Colin Nuckolls

  DOI：10.1021/ja0570786

  日期：2006.2.1

  This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were compared with DFT-optimized geometries. Both crystallographic and computed structures show that a planar acene core is the exception rather than the rule. In the assembly of these molecules, the phenyl groups block the herringbone motif and further guide the arrangement of the acene core into higher order structures. The packing for the phenyl-substituted derivatives is dictated by close contacts between the C-H's of the pendant aromatic rings and the carbons at the fusions in the acene backbone. Using thiciphene substituents instead of phenyls creates cofacially stacked acenes. In thin films, the thiophene-substituted derivative forms devices with good electrical properties: relatively high mobility, high ON/OFF ratios, and low threshold voltage for device activation. An unusual result is obtained for the decaphenyl pentacene when devices are fabricated on its crystalline surface. Although its acene cores are well isolated from each other, this material still exhibits good electrical properties.
• Stannylated α-pyrones: Synthesis, halogenation and destannylation reactions
  作者：Jürgen Sauer、Dieter K. Heldmann、Klaus-Jürgen Range、Manfred Zabel

  DOI：10.1016/s0040-4020(98)00754-6

  日期：1998.10

  inverse type [4+2] cycloadditions with various 1,3,4-oxadiazin-6-ones to afford two regioisomeric stannylated α-pyrones, which can be separated by flash column chromatography. Exposure of the stannanes to elemental halogens in chloroform or THF as solvent yields the corresponding halogeno pyrones. A general exception of this reaction type is also described. Destannylation with dry hydrogen chloride furnishes

  乙炔基三丁基锡与各种1,3,4-恶二嗪-6-酮进行逆型[4 + 2]环加成反应，得到两个区域异构的甲锡烷基化的α-吡喃酮，可通过快速柱色谱分离。将锡烷暴露于氯仿或THF中作为溶剂的元素卤素中，得到相应的卤代吡喃酮。还描述了该反应类型的一般例外。用干燥的氯化氢去甲锡烷基化可提供3，6-二取代的α-吡喃酮。