2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-3,4,6,6a,10a,10b-hexahydro-2-H-benzo[h]chromene-7,10-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-3,4,6,6a,10a,10b-hexahydro-2-H-benzo[h]chromene-7,10-dione
• 英文别名: (2R,6aS,10aS,10bS)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4,6,6a,10a,10b-hexahydro-2H-benzo[h]chromene-7,10-dione
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: QCWWWXPJQQLTHL-JSPVNYKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane 、 对苯醌 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-3,4,6,6a,10a,10b-hexahydro-2-H-benzo[h]chromene-7,10-dione
  参考文献：
  名称：

  A Facile Synthesis of Enantiopure Tricyclic Furanyl and Pyranyl Derivatives via Tungsten-Mediated Cycloalkenation and Diels−Alder Reaction

  摘要：

  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.

  DOI：

  10.1021/jo0205208

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.