3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one | 78460-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one
• 英文别名: 3,5-bis-((Ξ)-4-methoxy-benzylidene)-tetrahydro-pyran-4-one；3,5-Bis-((Ξ)-4-methoxy-benzyliden)-tetrahydro-pyran-4-on；3,5-Bis-(4-methoxy-benzyliden)-tetrahydro-pyran-4-on；3,5-Bis[(4-methoxyphenyl)methylidene]oxan-4-one
• CAS: 78460-52-3
• 化学式: C₂₁H₂₀O₄
• mdl: MFCD08547680
• 分子量: 336.387
• InChiKey: ADOXGRPZVZXSKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  565.4±50.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one 在 palladium on activated charcoal 、 乙二醇 作用下， 生成 3,5-bis-(4-methoxy-benzyl)-pyran-4-one
  参考文献：
  名称：

  γ-Pyrones by Isomerization. Substituted 3,5-Dibenzyl-4H-pyran-4-ones

  摘要：

  DOI：

  10.1021/ja01558a042
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one
  参考文献：
  名称：

  Borsche, Chemische Berichte, 1915, vol. 48, p. 684

  摘要：

  DOI：

文献信息

• First Highly Efficient Synthesis of bis(Arylmethylidene)pyranones Mediated by Lithium Perchlorate
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、M. Mehdi Zahedi、S. Mohammad Bolourtchian

  DOI：10.1080/00397910500334447

  日期：2006.2.1

  Abstract A remarkably efficient double‐crossed aldol condensation of tetrahydropyran‐4‐one with a variety of aromatic aldehydes is described at room temperature in the presence of (trimethylsilyl)diethylamine and lithium perchlorate under solvent‐free conditions. Excellent yields of 3,5‐bis(arylmethylidene)pyranones are achieved in a facile one‐pot general procedure.

  摘要 本文描述了在无溶剂条件下，在（三甲基甲硅烷基）二乙胺和高氯酸锂存在下，四氢吡喃-4-酮与多种芳香醛在室温下的非常有效的双交羟醛缩合反应。3,5-双（芳基亚甲基）吡喃酮的高产率是通过简单的一锅通用程序实现的。
• Tricyclic thiazolo[3,2-<i>a</i>]thiapyrano[4,3-<i>d</i>]pyrimidines and related analogs as potential anti-inflammatory agents
  作者：George Rovnyak、Virginia Shu、Joseph Schwartz

  DOI：10.1002/jhet.5570180219

  日期：1981.3

  A series of novel tricyclic thiazolo[3,2-a]thiapyrano[4,3-d]pyrimidines and related oxa, aza and carbo analogs of general formula 1 were prepared by a convenient addition-cyclization reaction involving 2-amino-2-thiazoline (4) and bisarylidene ketones of formula 3. Some of these compounds demonstrated antiinflammatory activity.

  通过方便的涉及2-氨基-2-的加成环化反应，制备了一系列新型的三环噻唑并[3,2- a ]噻并吡喃并[4,3- d ]嘧啶及相关的通式1的氧杂，氮杂和碳氧化合物。式3的噻唑啉（4）和双芳基酮。其中一些化合物具有抗炎活性。
• Three-Component [3 + 3] Heterocyclizations for Flexible Synthesis of Bicyclic Fused Pyridines Under Microwave Irradiation
  作者：Jie Liu、Yuan-Yuan Pan、Li-Yuan Xue、Wen-Juan Hao、Jin-Peng Zhang、Shu-Liang Wang、Bo Jiang

  DOI：10.1002/jhet.2438

  日期：2016.7

  Three‐component [3 + 3] heterocyclizations have been established under microwave irradiation, providing a flexible synthetic approach toward bicyclic fused pyridines. 3,5‐Dibenzylidenedihydro‐2H‐pyran‐4(3H)‐ones were subject with malononitrile and aromatic amines in cosolvent of HOAc and N,N‐dimethylformamide, affording 10 examples of pyrano[4,3‐b]pyridine derivatives in good to excellent yields. Similarly

  在微波辐射下已经建立了三组分[3 + 3]杂环，为双环稠合吡啶提供了灵活的合成方法。3,5-二苄基二氢-2 H-吡喃-4（3 H）-酮与丙二腈和芳香胺在HOAc和N，N-二甲基甲酰胺的共溶剂中共存，提供了10个吡喃并[4,3- b ]吡啶衍生物实例高产到高产。同样，使用硫拴系杂环作为反应伙伴，获得了七个硫吡喃并[4,3- b ]吡啶衍生物的实例。
• Molecular Iodine: An Efficient and Environment Friendly Catalyst for the Synthesis of 3,5-<i>Bis</i>-(arylmethylidene)-tetrahydropyran-4-ones
  作者：M. B. Madhusdana Reddy、Aatika Nizam、M. A. Pasha

  DOI：10.1080/00397910903531748

  日期：2010.11.16

  A rapid, efficient, convenient and cost-effective procedure has been developed for the synthesis of 3,5-bis-(arylmethylidene)-tetrahydropyran-4-ones by the condensation of tetrahydropyran-4-one with araldehydes in the presence of catalytic amount of iodine to obtain the products in good to excellent yield. The reactions work at 25 degrees C and go to completion within 30-60min.