2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-2,3,5,5a,9a,9b-hexahydronaphtho-[1,2-b]-furan-6,9-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-2,3,5,5a,9a,9b-hexahydronaphtho-[1,2-b]-furan-6,9-dione
• 英文别名: (2S,5aR,9aR,9bR)-2-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-2,3,5,5a,9a,9b-hexahydrobenzo[g][1]benzofuran-6,9-dione
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: ZMUFEIPBOXANAR-YYOLRRQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 zinc trifluoromethanesulfonate 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-2,3,5,5a,9a,9b-hexahydronaphtho-[1,2-b]-furan-6,9-dione
  参考文献：
  名称：

  Facile synthesis of enantiopure tricyclic furanyl derivatives via tungsten-mediated cycloalkenation reactions and Diels–Alder reactions

  摘要：

  Chiral furanyl diene 1 is easily prepared from cycloalkenation of chiral tungsten alkynol with acetaldehyde, followed by demetalation with Me3NO. This diene bears a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituent of the cycloadducts was degraded to a hydrogen atom to make these molecules possess a common furanyl functionality. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01815-4

文献信息

• A Facile Synthesis of Enantiopure Tricyclic Furanyl and Pyranyl Derivatives via Tungsten-Mediated Cycloalkenation and Diels−Alder Reaction
  作者：Heh-Lung Huang、Rai-Shung Liu

  DOI：10.1021/jo0205208

  日期：2003.2.1

  We report the synthesis of chiral furanyl and pyranyl dienes 1 and 2 based on cycloalkenation of chiral tungsten alkynol complexes. These two dienes bear a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituents of the cycloadducts were degraded into hydrogen atoms to make these molecules possess common furan and pyran rings. Dienes 1 and 2 are good building blocks for enantiopure forms of tricyclic oxygen compounds.
• Facile synthesis of enantiopure tricyclic furanyl derivatives via tungsten-mediated cycloalkenation reactions and Diels–Alder reactions
  作者：Heh-Lung Huang、Heh-Chang Huang、Rai-Shung Liu

  DOI：10.1016/s0040-4039(02)01815-4

  日期：2002.10

  Chiral furanyl diene 1 is easily prepared from cycloalkenation of chiral tungsten alkynol with acetaldehyde, followed by demetalation with Me3NO. This diene bears a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituent of the cycloadducts was degraded to a hydrogen atom to make these molecules possess a common furanyl functionality. (C) 2002 Elsevier Science Ltd. All rights reserved.