2,3-dihydro-2-methyl-2-phenyl-4H-furo[3,2-c][1]benzopyran-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: 2,3-dihydro-2-methyl-2-phenyl-4H-furo[3,2-c][1]benzopyran-4-one
• 英文别名: 2-methyl-2-phenyl-2,3-dihydro-4H-furo[3,2-c][1]benzopyran-4-one；2-methyl-2-phenyl-2,3-dihydro-4H-furo[3,2-c]chromen-4-one；2-methyl-2-phenyl-3H-furo[3,2-c]chromen-4-one
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: YOTPABIAGMRYST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-methyl-2-phenyl-4H-furo[3,2-c][1]benzopyran-4-one 在 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 以60%的产率得到2-methyl-3-phenyl-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  甲基烯醇醚的三氟化硼醚化物控制反应：二氢呋喃[3,2-c]色烯酮和呋喃[3,2-c]色烯酮衍生物的选择性合成

  摘要：

  提出了一种在无金属条件下通过甲基烯醇醚与 4-羟基香豆素反应来简便地一步合成二氢呋喃-[3,2- c ]色酮和呋喃[3,2 - c ]色酮的方法。通过控制三氟化硼乙醚合物的化学计量，选择性地得到二氢呋喃[3,2- c ]色酮和呋喃[3,2- c ]-色酮。据报道，芳基迁移后呋喃部分芳构化，导致各种呋喃[3,2- c ]色烯酮衍生物的收率良好。

  DOI：

  10.1055/a-1912-3884
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 氯仿 为溶剂， 生成 2,3-dihydro-2-methyl-2-phenyl-4H-furo[3,2-c][1]benzopyran-4-one
  参考文献：
  名称：

  Dihydrofurocoumarin and dihydrofurodihydropyrid-2-one derivatives via palladium catalysed cascades involving aryl/heteroaryl/vinyl iodides and allene followed by acid catalysed cyclisation

  摘要：

  Mono 3-(2'-arylallyl) derivatives of 4-hydroxycoumarin 1a,b, 4-hydroxy-6-methyl-pyran-2-one (3) and 6-hydroxy-1,4-dimethyl-1,2-dihydropyrid-2-one-3-carbonitrile (4) are produced in 3-component cascades involving aryl/heteroaryl/vinyl iodides and allene (1 atm) using Pd(PPh3)(4)/CS2CO3/MeCN/80degreesC or Pd-2(dba)(3)/tris(2-furyl)phosphine/K2CO3/DMF/80degreesC as the catalyst system. 4-Hydroxy-2-quinolone (2) afforded a mixture of mono- and bis-allylation products under these conditions. Mono C-allylation products 5a-e and 15a-e undergo facile acid catalysed cyclisation to afford dihydrofurocoumarins 11a-e and dihydrofurodihydropyrid-2-ones 16a-e in good overall yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.049

文献信息

• Synthesis of 2,3‐Dihydro‐4<i>H</i>‐furo[3,2‐c] chromen‐4‐ones and 2,3‐Dihydronaphtho[2,3‐b]furan‐4,9‐diones by the Radical Cyclizations of Hydroxyenones with Electron-Rich Alkenes using Manganese(III) Acetate
  作者：Mehmet Yılmaz、Mehtap Yakut、A. Tarık Pekel

  DOI：10.1080/00397910701845456

  日期：2008.2.1

  Abstract We have obtained dihydrofurans 3a–j in the radical cyclization of 4‐hydroxycoumarin 1a and 2‐hydroxy‐1,4‐naphtoquinone 1b with electron rich alkenes 2a–i by manganese(III) acetate. Methods A and B, which have different molar ratios were studied comparatively in these reactions, and we observed that method B (molar ratio 2:1:3) gave the best results. Treatment of 4‐hydroxycoumarin 1a and electron

  摘要 我们通过乙酸锰 (III) 对 4-羟基香豆素 1a 和 2-羟基-1,4-萘醌 1b 与富电子烯烃 2a-i 进行自由基环化反应获得了二氢呋喃 3a-j。在这些反应中对具有不同摩尔比的方法 A 和 B 进行了比较研究，我们观察到方法 B（摩尔比 2:1:3）给出了最好的结果。用方法 B 处理 4-羟基香豆素 1a 和富电子烯烃 2a-e 得到 2,3-二氢-4H-呋喃[3,2-c]色烯-4-酮 3a-e，产率为 36-86%。相同条件下，2-羟基-1,4-萘醌1b与共轭烯烃2b和2f-i反应得到2,3-二氢萘并[2,3-b]呋喃-4,9-二酮3f-j优良的产量。
• Studies on the Radical Cyclization of 3-Oxopropanenitriles and Alkenes with Cerium(IV) Ammonium Nitrate in Ether Solvents
  作者：Mehmet Yılmaz

  DOI：10.1002/hlca.201000440

  日期：2011.7

  1a–1e and alkenes 2a–2g with cerium(IV) ammonium nitrate (CAN) in ether solvents was investigated (Tables 1 and 2). In the optimization study, 1,3‐dioxolane, 1,4‐dioxane, 1,2‐dimethoxyethane, Et2O, and THF were used as ether‐based solvents, and the latter was found to be the most effective solvent in radical cyclizations mediated by cerium(IV). This system (cerium(IV)/THF) was applied to cyclizations

  对3-氧代丙烷腈1a - 1e和烯烃2a - 2g与硝酸铈（IV）铵（CAN）在醚溶剂中的自由基环化进行了研究（表1和表2）。在优化研究中，将1,3-二氧戊环，1,4-二氧六环，1,2-二甲氧基乙烷，Et 2 O和THF用作醚基溶剂，发现后者是自由基中最有效的溶剂。铈（IV）介导的环化。该系统（铈（IV）/ THF）用于各种3-氧代丙烷腈和1,3-二羰基化合物与烯烃的环化反应，从而以高收率形成4,5-二氢呋喃（表2和方案2））。将铈（IV）/ THF自由基环化的结果与乙酸锰（III）/ AcOH的结果进行了比较；事实证明，铈（IV）/ THF系统效率更高。
• Silver(I)/celite promoted oxidative cycloaddition of 4-hydroxycoumarin to olefins. A facile synthesis of dihydrofurocoumarins and furocoumarins
  作者：Yong Rok Lee、Byung So Kim、Han Cheol Wang

  DOI：10.1016/s0040-4020(98)00762-5

  日期：1998.10

  An efficient synthesis of dihydrofurocoumarins and furocoumarins is achieved from 4-hydroxycoumarins and olefins in the presence of Ag2CO3/Celite in moderate yields. The new method has been applied to the synthesis of the natural cyclobrachycoumarin isolated from Brachyclados megalanthus.

  在Ag 2 CO 3 / Celite存在下，由4-羟基香豆素和烯烃可以高效合成二氢呋喃香豆素和呋喃香豆素。该新方法已应用于合成自Brachyclados megalanthus的天然环水香豆素的合成。
• CAN-Mediated Oxidative Free Radical Reactions in an Ionic Liquid
  作者：Gregory Bar、Fabien Bini、Andrew F. Parsons

  DOI：10.1081/scc-120015703

  日期：2003.3

  Abstract Cerium(IV) ammonium nitrate-mediated oxidative radical reactions are carried out in the presence of ionic liquids, including 1-butyl-3-methylimidazolium tetrafluoroborate, for the first time. The presence of the ionic liquid not only increases the rate and yield of reactions in dichloromethane but also extends the range of 1,3-dicarbonyl precursors, which can be utilized in these carbon–carbon

  摘要 硝酸铈(IV)铵介导的氧化自由基反应首次在离子液体存在下进行，包括1-丁基-3-甲基咪唑鎓四氟硼酸盐。离子液体的存在不仅提高了二氯甲烷中反应的速率和产率，而且扩大了 1,3-二羰基前体的范围，可用于这些碳 - 碳键形成反应。
• Oxidative Addition of 4-Hydroxycoumarin to Alkenes. An Expeditious Entry to 2,3-Dihydro-4<i>H</i>-furo-[3,2-<i>c</i>][1]benzopyran-4-ones¹
  作者：Giovanni Appendino、Giancarlo Cravotto、Giovanni Palmisano、Rita Annunziata

  DOI：10.1080/00397919608003739

  日期：1996.9

  In the presence of one-electron metal oxidants (CAN, MAH), 4-hydroxycoumarin (1) adds to alkenes to give 2,3-dihydro-4H-furo[3,2-c][1]benzopyran-4-ones.