cis(3a,6a)-3-acetyl-2-methyl-3a,4,5,6a-tetrahydro-furo<2,3-b>furan | 135365-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: cis(3a,6a)-3-acetyl-2-methyl-3a,4,5,6a-tetrahydro-furo<2,3-b>furan
• 英文别名: cis-(3a,6a)-3-Acetyl-2-methyl-3a,4,5,6a-tetrahydrofuro[2,3-b]furan；cis(3a,6a)-3-acetyl-2-methyl-3a,4,5,6a-tetrahydro-furo[2,3-b]furan；1-[(3aS,6aR)-5-methyl-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-4-yl]ethanone
• CAS: 135365-42-3
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: GOELRTPKDANCAB-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,3-二氢呋喃 、 乙酰丙酮 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以68%的产率得到cis(3a,6a)-3-acetyl-2-methyl-3a,4,5,6a-tetrahydro-furo<2,3-b>furan
  参考文献：
  名称：

  硝酸铈铵介导的1,3-二羰基化合物与环状烯醇醚的环加成反应合成缩醛

  摘要：

  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。

  DOI：

  10.1016/0040-4020(96)00728-4

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 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。
• A direct synthesis of racemic demethoxyaflatoxin B2
  作者：George A. Kraus、Beth E. Johnston、Jacqueline M. Applegate

  DOI：10.1021/jo00019a042

  日期：1991.9

  Aflatoxin analogue 19 was prepared by a direct sequence involving a novel silver-mediated cyclization to 12, the Michael addition of 16 with 17, and the oxidation of the Michael addition adduct. The overall yield of this six-step route is approximately 11%. The pathway is a flexible one that will permit the synthesis of analogues for toxicological analysis.