8-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,6,7,8,9a,9b-hexahydro-3aH-2,9-dioxa-cyclopenta[a]naphthalene-1,3-dione | 496920-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,6,7,8,9a,9b-hexahydro-3aH-2,9-dioxa-cyclopenta[a]naphthalene-1,3-dione
• 英文别名: (2R,6aS,9aS,9bS)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4,6,6a,9a,9b-hexahydro-2H-furo[3,4-h]chromene-7,9-dione
• CAS: 496920-71-9
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: GJJJIXQHQNDJRZ-CKIKVBCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,6,7,8,9a,9b-hexahydro-3aH-2,9-dioxa-cyclopenta[a]naphthalene-1,3-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (2R,6aS,9aS,9bS)-2-((R)-1,2-Dihydroxy-ethyl)-3,4,6,6a,9a,9b-hexahydro-2H-furo[3,4-h]chromene-7,9-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
• 作为产物：
  描述：

  2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane 、 马来酸酐 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到8-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,6,7,8,9a,9b-hexahydro-3aH-2,9-dioxa-cyclopenta[a]naphthalene-1,3-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.