3-isopropyl-8a-methyl-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-6-ol | 1393526-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-isopropyl-8a-methyl-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-6-ol
• CAS: 1393526-86-7
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: KEGKRMFWBRJENJ-XWLWVQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (3S,4aS,8aR)-3-isopropyl-8a-methyl-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 生成 3-isopropyl-8a-methyl-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-6-ol 、 3-isopropyl-8a-methyl-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-6-ol
  参考文献：
  名称：

  An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Brønsted Acid Catalysis Cascade

  摘要：

  The desymmetrization of p-peroxyquinols using a Bronsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies, suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.

  DOI：

  10.1021/ja3052427