2-benzoyl-3-(4-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-benzoyl-3-(4-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
• 英文别名: trans-2-benzoyl-3-(p-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one；2-benzoyl-3-(p-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one；2-benzoyl-3-(p-methylphenyl)-2,3-dihydrofuro[3,2-c]chromen-4-one；(2S,3S)-2-benzoyl-3-(4-methylphenyl)-2,3-dihydrofuro[3,2-c]chromen-4-one
• 化学式: C₂₅H₁₈O₄
• 分子量: 382.416
• InChiKey: HDEOCOGYGFPDKJ-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 在 4-二甲氨基吡啶 、 苄基三乙基氯化铵 、 碘 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-benzoyl-3-(4-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Base-controlled selective construction of polysubstituted dihydrofuran and furan derivatives through an I2-mediated cyclization

  摘要：

  A base-controlled formal [3 + 2] cycloaddition of 1,3-dicarbonyl compounds to enones via an I-2-mediated cyclization was reported. Highly functionalized dihydrofurans and furans were selectively obtained under I-2/DMAP and I-2/DBU conditions in the cyclization step, respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.12.078

文献信息

• A Practical and Diastereoselective Synthesis of Dihydrofurocoumarin from Pyridinium Ylides in Aqueous Medium
  作者：Litao An、Xiaojun Sun、Lulu Zhang、Jianfeng Zhou、Fengxia Zhu、Zhengjia Shen

  DOI：10.3184/174751916x14768944130291

  日期：2016.11

  A series of 2,3-dihydrofurocoumarins were prepared via a three-component reaction of aldehyde, pyridinium salt and 4-hydroxycoumarin in aqueous ethanol. This method avoids using excessive pyridine and trimethylamine, and has operational simplicity and avoids tedious column chromatography purification. Both aryl aldehydes and aliphatic aldehydes are applicable to this protocol.

  通过醛、吡啶鎓盐和4-羟基香豆素在乙醇水溶液中的三组分反应制备了一系列2,3-二氢呋喃香豆素。该方法避免了使用过量的吡啶和三甲胺，操作简单，避免了繁琐的柱层析纯化。芳醛和脂肪醛均适用于本协议。
• Modified One-Pot Multicomponent Diastereoselective Synthesis of <i>Trans</i>-2,3-Dihydrofuro[3,2-c]coumarins via In Situ–Generated <font>α</font>-Tosyloxyketones
  作者：Ravi Kumar、Deepak Wadhwa、Khalid Hussain、Om Prakash

  DOI：10.1080/00397911.2012.671435

  日期：2013.7.3

  one-pot multicomoponent reaction starting from aromatic aldehydes, 4-hydroxycoumarin, and α-tosyloxyacetophenones with pyridine and triethylamine as catalysts. The developed protocol provides a better alternative to the existing methods as it involves utilization of α-tosyloxyacetophenones that may be generated in situ from acetophenones and [hydroxyl(tosyloxy)iodo]benzene (HTIB, Koser's reagent), avoiding

  摘要 通过从芳香醛、4-羟基香豆素和 α-甲苯磺酰氧基苯乙酮与吡啶开始的一锅多组分反应开发了一种用于非对映选择性合成不同取代的反式-2,3-二氢呋喃 [3,2-c] 香豆素的改进方案。和三乙胺作为催化剂。开发的协议为现有方法提供了更好的替代方案，因为它涉及利用可能从苯乙酮和 [羟基（甲苯磺酰氧基）碘] 苯（HTIB，Koser 试剂）原位生成的 α-甲苯磺酰苯乙酮，避免使用 α-卤代苯乙酮. 补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis of Functionalized Dihydrofurocoumarin Derivatives from 3-Aminoalkyl-4-hydroxycoumarin
  作者：Pallabi Borah、P. Seetham Naidu、Pulak J. Bhuyan

  DOI：10.1080/00397911.2015.1027405

  日期：2015.7.3

  Abstract Some dihydrofuro-fused coumarin derivatives were synthesized from 3-aminoalkyl-4-hydroxycoumarin via in situ generation of N-ylide. The 3-aminoalkylated 4-hydroxycoumarin derivatives were synthesized from one-pot, three-component reaction of 4-hydroxycoumarin, aryl aldehydes, and secondary amines in ethanol at room temperature. Again, when salicylaldehyde was employed instead of benzaldehyde

  摘要 以3-氨基烷基-4-羟基香豆素为原料，通过原位生成N-ylide合成了一些二氢呋喃稠合香豆素衍生物。3-氨基烷基化 4-羟基香豆素衍生物是由 4-羟基香豆素、芳基醛和仲胺在室温下在乙醇中的一锅三组分反应合成的。同样，当使用水杨醛代替苯甲醛时，有趣的是获得了吡喃香豆素。该反应方案可以进一步探索合成许多其他杂环稠合二氢呋喃。图形概要
• An efficient three-component approach for the diastereoselective synthesis of trans-2,3-dihydrofuran derivatives: an exceptional catalytic activity of SiO2 nanoparticles
  作者：Omekolsoom Sheibani、Sayed Hossein Banitaba

  DOI：10.1007/s11696-023-02822-3

  日期：2023.9

  reactions in the presence of solid nano-catalysts have attracted significant research interest in recent years. In this regard, a fast and operationally facile one-step tandem strategy for the diastereoselective synthesis of rel-(2R,3R)-2-benzoyl-2,3-dihydro-3-substitutedphenyl-4H-furo[3,2-c][1]benzopyran-4-one has been developed. This protocol has been applied via solvent-free condensation of aromatic aldehydes

  近年来，在固体纳米催化剂存在下进行有机反应引起了广泛的研究兴趣。在这方面，一种快速且操作简便的一步串联策略用于非对映选择性合成rel -(2R,3R)-2-benzoyl-2,3-dihydro-3-substitutedphenyl-4 H -furo[3,2- c][1]benzopyran-4-one 已开发。该协议已通过芳香醛、4-羟基香豆素和原位生成的苯甲酰溴化吡啶在 SiO 2上的无溶剂缩合得到应用纳米粒子作为非金属氧化物催化剂。该协议对环境有利，因为反应过程中不需要有机溶剂。此外，该方法快速、产率高、催化剂负载量低，而且不涉及大量的后处理程序或色谱分离。该催化剂价格低廉且非常温和，并且可以在六次运行中循环使用而不会显着降低活性。
• Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction
  作者：Elisa Altieri、Massimiliano Cordaro、Giovanni Grassi、Francesco Risitano、Angela Scala

  DOI：10.1016/j.tet.2010.10.023

  日期：2010.12

  An efficient and straightforward synthesis of furo[3 2-c]coumarins via the one-pot three-component condensation of aromatic aldehydes 4-hydroxycoumarin and alpha-chloroketones in refluxing n-propanol is described Pyridine or a mixture of AcOH and AcONH4 was used as a basic catalyst (C) 2010 Elsevier Ltd All rights reserved