2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane | 496920-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane
• 英文别名: (2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-ethenyl-3,4-dihydro-2H-pyran
• CAS: 496920-58-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PZCUOGBRWKCQPC-GHMZBOCLSA-N

物化性质

• 沸点：
  291.5±40.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane 在 盐酸 、 sodium periodate 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 1,3-dioxo-1,2,3,3a,4,6,7,8,9a,9b-decahydro-9-oxa-2-aza-cyclopenta[a]naphthalene-8-carbaldehyde
  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：

  alkaline earth salt of/the/ methylsulfuric acid 在 十二/十四烷基二甲基氧化胺 作用下， 以 乙腈 为溶剂， 生成 2-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-5-vinyl-3,4-dihydro-2H-pyrane
  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.