2-ethoxy-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one

• 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: 2-ethoxy-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
• 英文别名: 2-Ethoxy-6,6-dimethyl-2,3,6,7-tetrahydro-1-benzofuran-4(5h)-one；2-ethoxy-6,6-dimethyl-2,3,5,7-tetrahydro-1-benzofuran-4-one
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: XEEORBXWWMPMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  苄胺 、 2-ethoxy-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 在 对甲苯磺酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 18.0h， 以86%的产率得到1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one
  参考文献：
  名称：

  钌（II）催化的[3 + 2]环或无环重氮二羰基化合物与烯烃的环加成反应，高效一锅合成多取代的二氢呋喃

  摘要：

  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

  DOI：

  10.1002/adsc.201300245
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 对甲苯磺酰叠氮 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 11.0h， 生成 2-ethoxy-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
  参考文献：
  名称：

  钌络合物固定在功能化的针织超交联聚合物上，作为有机转化的高效可回收催化剂

  摘要：

  通过一步外部交联反应，由苯和三苯膦（PPh 3）制备了高交联聚合物（HCP）固定化钌催化剂（HCP-PPh 3 -Ru）。催化剂的结构和组成已通过许多物理化学方法得到了充分表征。发现HCP–PPh 3 –Ru具有较高的Brunauer–Emmett–Teller（BET）表面积，大孔体积和低骨骼密度。此外，Ru催化剂还具有一些优点，例如合成成本低以及良好的化学和热稳定性。然后，将HCP–PPh 3 –Ru用作可回收和有效的催化剂，用于从苯乙酮，乙酸铵（NH 4OAc）和二甲基甲酰胺（DMF），以及重氮二羰基化合物与烯烃的环加成反应，生成二氢呋喃。此外，HCP–PPh 3 –Ru和Amberlyst-15的组合使我们能够建立一个简单的协议，用于由重氮二羰基化合物，烷基乙烯基醚和吲哚直接合成咔唑衍生物。在这些选择的反应中，催化剂容易回收并重复使用数次而没有明显的活性损失。

  DOI：

  10.1002/adsc.201600816

文献信息

• Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues
  作者：Saqib Faisal、Qin Zang、Pradip K. Maity、Agnes Brandhofer、Patrick C. Kearney、Oliver Reiser、Robert N. Grass、Diana Stoianova、Paul R. Hanson

  DOI：10.1021/acs.orglett.7b00792

  日期：2017.5.5

  ROMP-derived benzenesulfonyl chloride and analogues is reported. The regeneration and utility of these reagents in the methylation/alkylation of various carboxylic acids is demonstrated via efficient retrieval of the magnetic reagent with a neodymium magnet. Additional reactions employing the analogue sulfonic acid and in situ generated magnetic benzenesulfonyl azide are also reported.

  报道了高负载，可循环利用的磁性Co / C杂化ROMP衍生的苯磺酰氯及其类似物的开发和应用。这些试剂在各种羧酸的甲基化/烷基化中的再生和实用性通过使用钕磁铁对磁性试剂的有效回收来证明。还报道了使用类似磺酸和原位生成的磁性苯磺酰基叠氮化物的其他反应。
• Alkylation of methylene-active compounds with halo acetals and hydrolysis of the alkylation products
  作者：V. M. Ismailov、N. N. Yusubov、N. D. Sadykhova、R. A. Gasymov、G. G. Ibragimova、I. A. Mamedov

  DOI：10.1134/s1070428016100031

  日期：2016.10

  A preparative procedure has been proposed for the alkylation of CH acids with halo acetals and hydrolysis of the alkylation products to furan derivatives and lactones.

  已经提出了用卤代缩醛将CH酸烷基化和将烷基化产物水解为呋喃衍生物和内酯的制备方法。
• KR2016/20022
  申请人：——

  公开号：——

  公开（公告）日：——
• [3+2]-Cycloaddition reactions of 2-phenyliodonio-5,5-dimethyl-1,3-dioxacyclohexanemethylide
  作者：Efstathios P Gogonas、Lazaros P Hadjiarapoglou

  DOI：10.1016/s0040-4039(00)01672-5

  日期：2000.11

  Iodonium ylide 2, derived from dimedone, undergoes thermal [3+2]-cycloaddition with acetylenes and nitriles with Rh-2(OAc)(4) to form the corresponding furans and oxazoles, respectively. Photochemically 2 reacts with various alkenes to form E-dihydrofuran derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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