(3aS,6S,6aR)-4-methoxy-6-methyltetrahydrofuro[3,4-b]furan-2(3H)-one | 1197132-95-8

• 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: (3aS,6S,6aR)-4-methoxy-6-methyltetrahydrofuro[3,4-b]furan-2(3H)-one
• 英文别名: (3aS,6S,6aR)-4-methoxy-6-methyl-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-2-one
• CAS: 1197132-95-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: MQFHOAUGAJSUKD-SWOGJVQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,6S,6aR)-4-methoxy-6-methyltetrahydrofuro[3,4-b]furan-2(3H)-one 在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 12.92h， 生成 (4S)-2-hexadecanyl-4-methylbut-2-enolide
  参考文献：
  名称：

  Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

  摘要：

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

  DOI：

  10.1021/ol503246k
• 作为产物：
  描述：

  甲醇 、 (1R,3S,5S,6R)-ethyl 4-hydroxy-3-methyl-2-oxa-bicyclo[3.1.0]hexane-6-carboxylate 在 硫酸 作用下， 反应 24.0h， 以69%的产率得到(3aS,6S,6aR)-4-methoxy-6-methyltetrahydrofuro[3,4-b]furan-2(3H)-one
  参考文献：
  名称：

  Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

  摘要：

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

  DOI：

  10.1021/ol503246k

文献信息

• Stereoselective Synthesis of Donor−Acceptor Substituted Cyclopropafuranones by Intramolecular Cyclopropanation of Vinylogous Carbonates: Divergent Synthesis of Tetrahydrofuran-3-one, Tetrahydropyran-3-one, and Lactones
  作者：Santosh J. Gharpure、Manoj K. Shukla、U. Vijayasree

  DOI：10.1021/ol902301h

  日期：2009.12.3

  A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbonate with carbenes using copper catalyst is described. Each of the cyclopropane bonds of these two acceptor substituted cyclopropafuranones can be cleaved with complete regiocontrol by judicious choice of reaction conditions, leading to a diverse array of frameworks such as tetra hydrofuran-3-one, tetrahydropyran-3-one, and lactones.
• Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide
  作者：Santosh J. Gharpure、Laxmi Narayan Nanda、Manoj Kumar Shukla

  DOI：10.1021/ol503246k

  日期：2014.12.19

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.