7,7-dimethyl-2,4-diphenyl-4,6,7,8-tetrahydro-5H-chromen-5-one | 84230-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-dimethyl-2,4-diphenyl-4,6,7,8-tetrahydro-5H-chromen-5-one
• 英文别名: 5H-1-Benzopyran-5-one, 4,6,7,8-tetrahydro-7,7-dimethyl-2,4-diphenyl-；7,7-dimethyl-2,4-diphenyl-6,8-dihydro-4H-chromen-5-one
• CAS: 84230-67-1
• 化学式: C₂₃H₂₂O₂
• 分子量: 330.426
• InChiKey: MXSDTCQTVYRNCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  504.6±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,5-dimethyl-2-(1,3-diphenyl-3-oxopropyl)-1,3-cyclohexanedione 在 phosphorus pentoxide 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 7,7-dimethyl-2,4-diphenyl-4,6,7,8-tetrahydro-5H-chromen-5-one
  参考文献：
  名称：

  Ahluwalia, V K; Kiran, Sushma; Aggarwal, R, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 12, p. 1095 - 1097

  摘要：

  DOI：

文献信息

• Magnetically recoverable silica catalysed solvent-free domino Knoevenagel-hetero-Diels–Alder reaction to access divergent chromenones
  作者：Mrinaly Suri、Farhaz Liaquat Hussain、Chinu Gogoi、Pankaj Das、Pallab Pahari

  DOI：10.1039/d0ob00284d

  日期：——

  component DKHDA reaction involving 1,3-dicarbonyl, ketones, and alkynes producing spirocyclic pyranone derivatives. Twenty-six different highly substituted chromenones were synthesized using this methodology. A wide substrate scope due to the multicomponent nature of the reaction, high atom economy, the use of inexpensive and non-toxic recyclable silica as the catalyst, and solvent free reaction conditions

  据报道，1，3-二羰基，醛/酮和烯烃/炔烃之间存在三组分的多米诺Knoevenagel-杂-Diels-Alder（DKHDA）反应，导致色酮，二氢色酮和螺环色酮的合成不同。反应是在无溶剂条件下使用可磁分离的二氧化硅（Fe 3 O 4 @SiO 2）催化剂。尽管已知两种组分的DKHDA反应，但这是涉及产生螺环吡喃酮衍生物的1，3-二羰基，酮和炔烃的三组分DKHDA反应的第一个例子。使用该方法合成了二十六个不同的高度取代的色农酮。由于反应的多组分性质，高原子经济性，使用廉价且无毒的可回收二氧化硅作为催化剂以及无溶剂反应条件，因此底物范围广，使其成为一种有利的工艺。使用不同的分析技术（例如XRD，IR，HRTEM，VSM和TGA）对催化剂进行了表征。根据早期的报告，还提出了一种机制。
• Preparation of Pyran Derivatives Promoted by FeCl₃·6H₂O in Ionic Liquid
  作者：Xinying Zhang、Quanjian Lv、Xuesen Fan、Guirong Qu

  DOI：10.3184/030823408x324715

  日期：2008.6

  The condensation reaction of chalcone and 1,3-cyclohexanedione was smoothly carried out in [bmim][BF₄] with catalysis by FeCl₃·6H₂O. A series of substituted pyrans were obtained by this reaction, in high yields under mild conditions through a simple operational procedure. In addition, the ionic liquid together with the catalyst used can be conveniently recovered and efficiently reused.

  在 FeCl3-6H2O 催化下，查尔酮和 1,3-环己二酮在 [bmim][BF4] 中顺利进行了缩合反应。该反应通过简单的操作步骤，在温和的条件下获得了一系列高产率的取代吡喃。此外，所使用的离子液体和催化剂可以方便地回收和有效地重复使用。
• Two‐Step Sequence Multicomponent Synthesis/Reductive Rearrangement of 2‐Acyl‐2,3‐dihydrofurans for Modular Assembly of Annulated 4 <i>H</i> ‐Pyrans
  作者：Maxim R. Demidov、Dmitry V. Osipov、Konstantin A. Korol'kov、Vitaly A. Osyanin

  DOI：10.1002/adsc.202100261

  日期：2021.8.3

  readily available structurally diverse precursors and then rearranged into a series of annulated 4H-pyrans by the action of Sm/TMSCl or Zn/ZrCl4 redox systems. Present synthetic sequence is claimed as a modular approach to hetero- and carbon-fused 4H-pyrans. The rearrangement involves the SET reduction of carbonyl group to carbene followed by rare type of [1,2]-aroxyl shift. Synthetic toolbar was enriched

  各种反式-2-酰基-2,3-二氢呋喃已由易于获得的结构多样的前体组装而成，然后在 Sm/TMSCl 或 Zn/ZrCl 4氧化还原系统的作用下重新排列成一系列环状4 H-吡喃。目前的合成序列被认为是杂-和碳-稠合 4 H-吡喃的模块化方法。重排涉及羰基的 SET 还原为卡宾，然后是罕见的 [1,2]-芳氧基转移。使用 Zn/ZrCl 4氧化还原系统丰富了合成工具栏。
• Solvent-free synthesis of 5-oxo-5,6,7,8-tetrahydro-4<i>H</i>-benzo-[<i>b</i>]-pyran derivatives under microwave irradiation
  作者：Xue Yuan Hu、Xue Sen Fan、Xin Ying Zhang、Gui Rong Qu、Yan Zhen Li

  DOI：10.1139/v06-132

  日期：2006.8.1

  Several benzo-[b]-pyran derivatives were prepared via microwave irradiation under solvent-free conditions in the presence of InCl₃·4H₂O. The advantages of this method include simple operational process, environmental benignancy, and high efficiency. Moreover, the catalyst can be recovered and reused effectively for at least six times.Key words: benzo-[b]-pyran derivatives, indium trichloride, microwave irradiation.

  在 InCl3-4H2O 存在的无溶剂条件下，通过微波辐照制备了多种苯并-[b]-吡喃衍生物。这种方法的优点是操作过程简单、对环境无害、效率高。关键词：苯并[b]-吡喃衍生物；三氯化铟；微波辐照。
• InBr3-catalyzed annulations of cyclic 1,3-diketones with aryl propargyl alcohols: a novel synthesis of 2,4-diaryldihydropyrans
  作者：J.S. Yadav、B.V. Subba Reddy、K.V. Raghavendra Rao、R. Narender

  DOI：10.1016/j.tetlet.2009.04.088

  日期：2009.7

  The cyclic 1,3-dicarbonyl compounds undergo smooth cyclization with aryl propargyl alcohols in the presence of 10 mol % indium tribromide in refluxing dichloroethane to produce 2,4-diarylpyran derivatives in good yields with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.