3,4-dihydroxy-4-methylcyclohexanone | 1393526-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxy-4-methylcyclohexanone
• 英文别名: (3S,4R)-3,4-dihydroxy-4-methylcyclohexan-1-one
• CAS: 1393526-83-4
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: YIIRQWMGNWRVKA-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-isopropyl-8a-methyltetrahydrobenzo[e][1,2,4]trioxin-6(7H)-one 在 溶剂黄146 、 锌 作用下， 反应 6.0h， 以85%的产率得到3,4-dihydroxy-4-methylcyclohexanone
  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