(1aR,2S,5R,5aS)-2,5-diisopropylperhydrooxireno[2,3-d][1,2]dioxine | 570393-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1aR,2S,5R,5aS)-2,5-diisopropylperhydrooxireno[2,3-d][1,2]dioxine
• 英文别名: (1R,2S,5R,6S)-2,5-di(propan-2-yl)-3,4,7-trioxabicyclo[4.1.0]heptane
• CAS: 570393-86-1
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: SKGWAPHUQSHBFK-YNFQOJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1aR,2S,5R,5aS)-2,5-diisopropylperhydrooxireno[2,3-d][1,2]dioxine 在 N,N'-bis(salicylidene)ethylenediaminocobalt(II) 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(+/-)-(1aS,4S,4aR)-2,4-diisopropyltetrahydrooxireno[2,3-c]furan-2-ol
  参考文献：
  名称：

  Base- and Co(II)-Catalyzed Ring-Opening Reactions of Perhydrooxireno[2,3-d][1,2]dioxines:  An Efficient Route to 4-Hydroxy-2,3-epoxy-ketones

  摘要：

  A series of 3,4,6-substituted 3,6-dihydro-1,2-dioxines were epoxidized with m-chloroperbenzoic acid to furnish perhydrooxireno[2,3-d][1,2]dioxines (epoxy- 1,2-dioxines) in yields ranging from 51% to 93% with de's from 26% to 100%. Unsymmetrical epoxy- 1,2-dioxines were ring-opened using triethylamine to yield 4-hydroxy-2,3-epoxy-ketones quantitatively, and meso-epoxy-1,2-dioxines were ring-opened using Co(II) salen complexes to afford 4-hydroxy-2,3-epoxy-ketones in 77-98% yield. The first reported examples of the catalytic asymmetric ring-opening of meso-epoxy-1,2-dioxines using a range of chiral Co(II) salen and beta-ketoiminato complexes to afford highly enantio-enriched 4-hydroxy-2,3-epoxy-ketones are also presented.

  DOI：

  10.1021/jo0300845
• 作为产物：
  描述：

  (3S,6R)-3,6-Diisopropyl-3,6-dihydro-[1,2]dioxine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1aR,2S,5R,5aS)-2,5-diisopropylperhydrooxireno[2,3-d][1,2]dioxine 、 (1aR,2R,5S,5aS)-2,5-diisopropylperhydrooxireno[2,3-d][1,2]dioxine
  参考文献：
  名称：

  Base- and Co(II)-Catalyzed Ring-Opening Reactions of Perhydrooxireno[2,3-d][1,2]dioxines:  An Efficient Route to 4-Hydroxy-2,3-epoxy-ketones

  摘要：

  A series of 3,4,6-substituted 3,6-dihydro-1,2-dioxines were epoxidized with m-chloroperbenzoic acid to furnish perhydrooxireno[2,3-d][1,2]dioxines (epoxy- 1,2-dioxines) in yields ranging from 51% to 93% with de's from 26% to 100%. Unsymmetrical epoxy- 1,2-dioxines were ring-opened using triethylamine to yield 4-hydroxy-2,3-epoxy-ketones quantitatively, and meso-epoxy-1,2-dioxines were ring-opened using Co(II) salen complexes to afford 4-hydroxy-2,3-epoxy-ketones in 77-98% yield. The first reported examples of the catalytic asymmetric ring-opening of meso-epoxy-1,2-dioxines using a range of chiral Co(II) salen and beta-ketoiminato complexes to afford highly enantio-enriched 4-hydroxy-2,3-epoxy-ketones are also presented.

  DOI：

  10.1021/jo0300845