(3S,4aS,8aR)-8a-methyl-3-(3-methylisoxazol-5-yl)-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one | 1393526-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4aS,8aR)-8a-methyl-3-(3-methylisoxazol-5-yl)-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one
• 英文别名: (3S,4aS,8aR)-8a-methyl-3-(3-methyl-1,2-oxazol-5-yl)-4a,5-dihydro-1,2,4-benzotrioxin-6-one
• CAS: 1393526-71-0
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: GNJWHPVEBQQGHL-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基异恶唑-5-甲醛 、 4-hydroperoxy-4-methylcyclohexa-2,5-dien-1-one 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-phenylthiourea 、 (Ra)-12-hydroxy-1,10-bis(2,4,6-triisopropylphenyl)-4,5,6,7-tetrahydrodiindeno[1,3,2]dioxaphosphocine 12-oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 以53%的产率得到(3S,4aS,8aR)-8a-methyl-3-(3-methylisoxazol-5-yl)-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one
  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

文献信息

• An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Brønsted Acid Catalysis Cascade
  作者：David M. Rubush、Michelle A. Morges、Barbara J. Rose、Douglas H. Thamm、Tomislav Rovis

  DOI：10.1021/ja3052427

  日期：2012.8.22

  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.