2-benzoyl-3-(4-chlorophenyl)-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-chlorophenyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
• 英文别名: (2S,3S)-2-benzoyl-3-(4-chlorophenyl)-2,3-dihydrofuro[3,2-c]chromen-4-one
• 化学式: C₂₄H₁₅ClO₄
• 分子量: 402.834
• InChiKey: UTGRUJDTXBRHMA-CVDCTZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-氯查耳酮 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-chlorophenyl)-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 concise synthesis of furo[3,2-c]coumarins catalyzed by nanocrystalline ZnZr4(PO4)6 ceramics under microwave irradiation
  作者：Javad Safaei-Ghomi、Pouria Babaei、Hossein Shahbazi-Alavi、Stephen G. Pyne、Anthony C. Willis

  DOI：10.1007/s13738-016-0859-1

  日期：2016.8

  A simple and concise method catalyzed by nanocrystalline ZnZr4(PO4)6 ceramics has been reported for the synthesis of a series of trans-2-benzoyl-3-(aryl)-2H-furo[3,2-c]chromen-4(3H)-ones using a multicomponent reaction of 2,4′-dibromoacetophenone, benzaldehydes and 4-hydroxycoumarin under microwave irradiation. This method provides several advantages including easy workup, excellent yields, short reaction

  纳米晶ZnZr 4（PO 4）6陶瓷催化的一种简单简便的方法已被报道用于合成一系列反式-2-苯甲酰基-3-（芳基）-2 H-呋喃[3,2-c]铬-4（3H）-在微波辐射下使用2,4'-二溴苯乙酮，苯甲醛和4-羟基香豆素的多组分反应。该方法具有许多优点，包括易于后处理，优异的产率，较短的反应时间，使用微波作为清洁方法，催化剂的可回收性和催化剂负载量小。
• 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。
• Aqueous Iodine(III)-Mediated Stereoselective Oxidative Cyclization for the Synthesis of Functionalized Fused Dihydrofuran Derivatives
  作者：Yang Ye、Linfei Wang、Renhua Fan

  DOI：10.1021/jo902553k

  日期：2010.3.5

  An efficient aqueous oxidative cyclization mediated by the combination of iodosobenzene with tetra-(n-butyl)ammonium iodide provides a new convenient and useful route to functionalized fused dihydrofuran derivatives in moderate to excellent yields with high diastereoselectivities.

  由碘代苯与碘化四（正丁基）铵的结合介导的有效的水性氧化环化提供了一种新的方便且有用的途径，以中等至极好的收率和高的非对映选择性来官能化稠合的二氢呋喃衍生物。
• 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