1,3-dioxo-2-phenyl-1,2,3,3a,4,6,7,8,9a,9b-decahydro-9-oxa-2-azacyclopenta[a]naphthalene-8-carbaldehyde | 496920-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,3-dioxo-2-phenyl-1,2,3,3a,4,6,7,8,9a,9b-decahydro-9-oxa-2-azacyclopenta[a]naphthalene-8-carbaldehyde
• CAS: 496920-96-8
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: VJTAJFBWHOIAIM-FXUDXRNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-dioxo-2-phenyl-1,2,3,3a,4,6,7,8,9a,9b-decahydro-9-oxa-2-azacyclopenta[a]naphthalene-8-carbaldehyde 在 RhCl(PPh₃)3 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到2-phenyl-4,6,7,8,9a,9b-hexahydro-3aH-9-oxa-2-azacyclopenta[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
• 作为产物：
  描述：

  (2R,6aS,9aS,9bS)-2-((R)-1,2-Dihydroxy-ethyl)-8-phenyl-3,4,6,6a,9a,9b-hexahydro-2H-pyrano[2,3-e]isoindole-7,9-dione 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50 mg的产率得到1,3-dioxo-2-phenyl-1,2,3,3a,4,6,7,8,9a,9b-decahydro-9-oxa-2-azacyclopenta[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