cis-(4a,9a)-7,7-Dimethyl-3,4,4a,5,6,7,8,9a-octahydro-2H-pyrano[2,3-b]benzofuran-5-one | 139061-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: cis-(4a,9a)-7,7-Dimethyl-3,4,4a,5,6,7,8,9a-octahydro-2H-pyrano[2,3-b]benzofuran-5-one
• 英文别名: cis(4a,9a)-7,7-dimethyl-3,4,4a,5,6,7,8,9a-octahydro-2H-pyrano<2,3-b>benzofuran-5-one；7,7-dimethyl-4,4a,6,7,8,9a-hexahydro-2H-pyrano[2,3-b]-benzofuran-5(3H)-one；(4aS,9aR)-7,7-dimethyl-3,4,4a,6,8,9a-hexahydro-2H-pyrano[2,3-b][1]benzofuran-5-one
• CAS: 139061-25-9
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: AOSWTTOQCQWOMR-QPUJVOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 2-重氮基-5,5-二甲基-1,3-环己二酮 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以82%的产率得到cis-(4a,9a)-7,7-Dimethyl-3,4,4a,5,6,7,8,9a-octahydro-2H-pyrano[2,3-b]benzofuran-5-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

文献信息

• Synthesis of fused acetal derivatives by manganic acetate promoted additions to endocyclic enol ethers
  作者：John M. Mellor、Shahid Mohammed

  DOI：10.1016/s0040-4020(01)87230-6

  日期：1993.8

  Reaction of manganic acetate in acetic acid with β-diketones and β-ketoesters leads to generation of intermediates, which add efficiently to endocyclic unsaturated enol ethers to afford fused acetals.

  乙酸锰在乙酸中与β-二酮和β-酮​​酸酯的反应导致生成中间体，该中间体可有效地添加到环内不饱和烯醇醚中以提供稠合缩醛。
• Tetrabutylammonium Peroxydisulfate in Organic Synthesis; IX: A Convenient Approach to the Synthesis of Fused Acetal Derivatives by Tetrabutylammonium Peroxydisulfate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Cyclic Enol Ethers
  作者：Fen-Er Chen、Han Fu、Ge Meng、Yu Cheng、Ye-Li Hu

  DOI：10.1055/s-2000-6312

  日期：——

  A number of fused acetal derivatives were prepared in 82-90% yield by tetrabutylammonium peroxydisulfate-mediated oxidative cycloaddition of 1,3-diketones or 1,3-diketoesters to cyclic enol ethers in the presence of a base such as potassium acetate in acetonitrile.

  通过四丁基过氧化二硫酸铵介导的 1,3-二酮或 1,3-二酮酯与环状烯醇醚在乙腈中的氧化环化反应，制备出了一些融合缩醛衍生物，收率为 82-90%。
• Synthesis of fused acetals by ceric ammonium nitrate mediated cycloaddition of 1,3-dicarbonyl compounds to cyclic enol ethers
  作者：Subhas Chandra Roy、Pijus Kumar Mandal

  DOI：10.1016/0040-4020(96)00728-4

  日期：1996.9

  Treatment of β-diketones and β-ketoesters with ceric ammonium nitrate and sodium hydrogen carbonate in acetonitrile leads to the formation of intermediates which add efficiently to cyclic enol ethers to furnish fused acetals in good yields.

  用硝酸铈铵和碳酸氢钠在乙腈中处理β-二酮和β-酮​​酸酯会导致形成中间体，该中间体可有效地添加到环状烯醇醚中，从而以高收率提供熔融缩醛。
• Synthesis of oxygen spirocycles by manganic acetate promoted additions to exocyclic enol ether derivatives
  作者：John M. Mellor、Shahid Mohammed

  DOI：10.1016/0040-4039(91)85053-8

  日期：1991.11

  Oxidative addition, promoted by manganic acetate, of β-dicarbonyl compounds to enol lactones and related enol derivatives having an exocyclic double bond affords spirocyclic products, and addition to endocyclic enol ethers gives fused acetals and ketals.

  由乙酸锰促进的β-二羰基化合物氧化加成至烯醇内酯和具有环外双键的相关烯醇衍生物可得到螺环产物，而加到环内烯醇醚上则可得到缩合缩醛和缩酮。
• 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