2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-dione | 496920-62-8

• 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: 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-dione
• 英文别名: (2S,5aR,8aR,8bR)-2-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-7-phenyl-2,3,5,5a,8a,8b-hexahydrofuro[2,3-e]isoindole-6,8-dione
• CAS: 496920-62-8
• 化学式: C₂₉H₃₁NO₆
• 分子量: 489.568
• InChiKey: LILNKMZSRSURFN-OSZANLPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2R,5aR,8aR,8bR)-2-((1R,2S)-3-Benzyloxy-1,2-dihydroxy-propyl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-furo[2,3-e]isoindole-6,8-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：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 锌 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-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.