2-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)-2,3,4,4a,8a,8b-hexahydro-1,7-dioxa-as-indacene-6,8-dione | 496920-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)-2,3,4,4a,8a,8b-hexahydro-1,7-dioxa-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]-2,3,5,5a,8a,8b-hexahydrofuro[3,4-g][1]benzofuran-6,8-dione
• CAS: 496920-56-0
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: YVPPONTVCJOPCJ-JIFZMYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)-2,3,4,4a,8a,8b-hexahydro-1,7-dioxa-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)-2,3,5,5a,8a,8b-hexahydro-benzo[2,1-b;3,4-c']difuran-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：

  马来酸酐 、 4-benzyloxymethyl-2,2-dimethyl-5-(4-vinyl-2,3-dihydrofuran-2-yl)[1,3]dioxolane 以 甲苯 为溶剂， 反应 12.0h， 以84%的产率得到2-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)-2,3,4,4a,8a,8b-hexahydro-1,7-dioxa-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