4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-yl acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-yl acetate
• 英文别名: 2-acetoxy-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；(4-oxo-3,5,6,7-tetrahydro-2H-1-benzofuran-2-yl) acetate
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: WLTIXLURAIUHQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-yl acetate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以81%的产率得到6,7-二氢-4(5H)-苯并呋喃酮
  参考文献：
  名称：

  AgBF4/[Bmim]BF4 催化的环状重氮二羰基化合物的 [3+2] 环加成：高效合成 2,3-二氢呋喃并转化为 3-酰基呋喃

  摘要：

  通过环状重氮二羰基化合物与苯乙烯和乙酸乙烯酯的反应，实现了一种新型高效的二氢呋喃环上具有多种取代基的 2,3-二氢呋喃的合成方法。关键策略是 AgBF/[Bmim]BF 催化的 [3+2] 环加成。合成的具有乙酸根的二氢呋喃进一步转化为相应的 3-酰基呋喃。

  DOI：

  10.5012/bkcs.2011.32.5.1554
• 作为产物：
  描述：

  1,3-环己二酮 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-yl acetate
  参考文献：
  名称：

  Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes

  摘要：

  The one-pot, three-component reactions of substituted 1,3-cyclohexanediones, iodobenzene diacetate and alkenes, under photochemical activation, yields fused dihydrofuran derivatives in good yield via the in situ formation of iodonium ylides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.006

文献信息

• A concise new synthesis of angular furanocoumarins: Angelicin, oroselone & oroselol
  作者：Yong Rok Lee

  DOI：10.1016/0040-4020(95)00070-o

  日期：1995.3

  An efficient synthesis of angular furanocoumarins has been carried out starting from dihydrobenzofuran derivatives.
• Efficient One-Pot Synthesis of Multi-Substituted Dihydrofurans by Ruthenium(II)-Catalyzed [3+2] Cycloaddition of Cyclic or Acyclic Diazodicarbonyl Compounds with Olefins
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1002/adsc.201300245

  日期：2013.8.12

  AbstractRuthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate Ru(PPh3)3Cl2/[Bmim]BF4}‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.magnified image
• A new route for the synthesis of furanoflavone and furanochalcone natural products
  作者：Yong Rok Lee、Andrew T. Morehead

  DOI：10.1016/0040-4020(95)98689-f

  日期：1995.4

  An efficient synthesis of furanoflavones and furanochalcones has been carried out starting from a dihydrobenzofuran derivative.
• Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes
  作者：Dimitra Kalpogiannaki、Catherine-Irene Martini、Aggeliki Nikopoulou、John A. Nyxas、Vassiliki Pantazi、Lazaros P. Hadjiarapoglou

  DOI：10.1016/j.tet.2012.12.006

  日期：2013.2

  The one-pot, three-component reactions of substituted 1,3-cyclohexanediones, iodobenzene diacetate and alkenes, under photochemical activation, yields fused dihydrofuran derivatives in good yield via the in situ formation of iodonium ylides. (C) 2012 Elsevier Ltd. All rights reserved.
• AgBF₄/[Bmim]BF₄-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans
  作者：Likai Xia、Yong-Rok Lee、Sung-Hong Kim、Won-Seok Lyoo

  DOI：10.5012/bkcs.2011.32.5.1554

  日期：2011.5.20

  A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF/[Bmim]BF-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.

  通过环状重氮二羰基化合物与苯乙烯和乙酸乙烯酯的反应，实现了一种新型高效的二氢呋喃环上具有多种取代基的 2,3-二氢呋喃的合成方法。关键策略是 AgBF/[Bmim]BF 催化的 [3+2] 环加成。合成的具有乙酸根的二氢呋喃进一步转化为相应的 3-酰基呋喃。