4H-furo[3,2-c]chromen-4-one | 2290-09-7

• 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: 4H-furo[3,2-c]chromen-4-one
• 英文别名: furo[3,2-c]chromen-4-one；furo[3,2-c]chromen-4-one
• CAS: 2290-09-7
• 化学式: C₁₁H₆O₃
• mdl: MFCD01443927
• 分子量: 186.167
• InChiKey: PJSRBPQIBGEFRC-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  336.6±11.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4H-furo[3,2-c]chromen-4-one 、 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 在 triple carbon acid 1c 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以75%的产率得到(Z)-ethyl 2-(4H-furo[3,2-c]chromen-4-ylidene)acetate
  参考文献：
  名称：

  Organic acid induced olefination reaction of lactones

  摘要：

  通过含有双(triflyl)甲基作为酸性官能团的碳酸（C–H酸）催化，实现了几种内酯与酮烯丙基乙酯的 (Z)-选择性烯化；尤其是具有三个双(triflyl)甲基的三重碳酸的苯酚磷酸在催化性能上表现出色。

  DOI：

  10.1039/c2cc33606e
• 作为产物：
  描述：

  methyl 2-(2-chlorophenyl)furan-3-carboxylate 在 噻吩-2-甲酸亚铜(I) 、 四甲基乙二胺 、 caesium carbonate 作用下， 以 水 为溶剂， 300.0 ℃ 、1.72 MPa 条件下， 反应 0.17h， 以30%的产率得到4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C

  摘要：

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.045

文献信息

• 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。
• Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: synthesis of dihydrofuran derivatives
  作者：Zi-cong Chen、Lang Tong、Zhi-bo Du、Zhi-feng Mao、Xue-jing Zhang、Yong Zou、Ming Yan

  DOI：10.1039/c8ob00293b

  日期：——

  A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

  通过β-萘酚和4-羟基香豆素与乙烯基ulf盐的环化反应，开发了一种新的合成二氢呋喃衍生物的方法。在温和的条件下以中等至良好的产率制备了多种二氢呋喃衍生物。通过用DDQ脱氢，可以容易地将产物转化为相应的呋喃。
• One pot synthesis of bioactive benzopyranones through palladium-catalyzed C–H activation and CO insertion into 2-arylphenols
  作者：Tai-Hua Lee、Jayachandran Jayakumar、Chien-Hong Cheng、Shih-Ching Chuang

  DOI：10.1039/c3cc47197g

  日期：——

  Palladium-catalyzed oxidative carbonylation of 2-arylphenols through C-H bond activation and C-C and C-O bond formation under acid-base free and mild conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important benzopyranone derivatives in up to 87% isolated yield.

  已经开发了在无酸碱和温和条件下通过CH键活化以及CC和CO键形成的钯催化的2-芳基苯酚的氧化羰基化反应。该反应可耐受多种底物，并以高达87％的分离产率提供生物学上重要的苯并吡喃酮衍生物。
• Majumdar, Krishna C.; Bhattacharyya, Trijit, Journal of Chemical Research, Miniprint, 1997, # 7, p. 1701 - 1707
  作者：Majumdar, Krishna C.、Bhattacharyya, Trijit

  DOI：——

  日期：——
• Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins
  作者：Gang Cheng、Youhong Hu

  DOI：10.1021/jo800439y

  日期：2008.6.1

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.