2-benzoyl-3-(4-methoxyphenyl)-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-methoxyphenyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
• 英文别名: (2S,3S)-2-benzoyl-3-(4-methoxyphenyl)-2,3-dihydrofuro[3,2-c]chromen-4-one
• 化学式: C₂₅H₁₈O₅
• 分子量: 398.415
• InChiKey: NAJVZXSQGCTBMS-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基查耳酮 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-methoxyphenyl)-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。
• Facile ionic liquid-mediated, three-component sequential reactions for the green, regio- and diastereoselective synthesis of furocoumarins
  作者：Stephen Michael Rajesh、Subbu Perumal、J. Carlos Menéndez、Sokkar Pandian、Ramachandran Murugesan

  DOI：10.1016/j.tet.2012.04.058

  日期：2012.7

  An environmentally friendly approach to the diastereoselective synthesis of trans-4-oxo-3-aryl-3,4-dihydro-2H-furo[3,2-c]coumarin-2-carbonitriles, trans-2-benzoyl-3-(aryl)-2H-furo[3,2-c]chromen-4(3H)-ones and trans-ethyl-4-oxo-3-(aryl)-3,4-dihydro-2H-furo[3,2-c]chromene-2-carboxylates in good yields is described. The method is based on the sequential multicomponent reactions of 4-hydroxycoumarin, aromatic

  反式-4-氧代-3-芳基-3,4-二氢-2 H-呋喃并[3,2 - c ]香豆素-2-腈，反式-2-苯甲酰基-3-非对映选择性合成的环保方法（芳基）-2 H-呋喃[3,2 - c ] chromen-4（3 H）-ones和反-乙基-4-氧代-3-（芳基）-3,4-二氢-2 H-呋喃[描述了高产率的3，2 - c ]亚甲基-2-羧酸酯。该方法基于4-羟基香豆素，芳香醛和原位的顺序多组分反应 在离子液体[BMIm] OH的存在下生成氰基甲基吡啶鎓，苯并吡啶基吡啶鎓/（2-乙氧基-2-氧乙基）吡啶鎓叶立德，其既起催化剂作用，又起反应介质的作用。
• 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
• 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
• Diastereoselective Synthesis of <i>trans</i>-2,3-Dihydrofurans with Pyridinium Ylide Assisted Tandem Reaction
  作者：Qi-Fang Wang、Hong Hou、Li Hui、Chao-Guo Yan

  DOI：10.1021/jo901379h

  日期：2009.10.2

  An efficient synthetic procedure for the preparation of fused 2,3-dihydrofuran derivatives was developed with the assistance of pyridinium ylide. A sequential one-pot, two-step tandem reaction starting from pyridine, aromatic aldehyde, dimedone, or 4-hydroxycoumarin and alpha-phenacyl bromide or p-nitrobenzyl bromide with triethylamine as catalyst proceeded smoothly in acetonitrile. H-1 NMR spectroscopy and single-crystal analysis demonstrated that the obtained 2,3-dihydrofurans are trans isomers.