2-(3-((3S,4aS,8aR)-8a-methyl-6-oxo-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-3-yl)propyl)isoindoline-1,3-dione | 1393526-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(3-((3S,4aS,8aR)-8a-methyl-6-oxo-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-3-yl)propyl)isoindoline-1,3-dione
• 英文别名: 2-[3-[(3S,4aS,8aR)-8a-methyl-6-oxo-4a,5-dihydro-1,2,4-benzotrioxin-3-yl]propyl]isoindole-1,3-dione
• CAS: 1393526-66-3
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: CNZQFSHBKFKZRX-TXPKVOOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁醛 、 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81%的产率得到2-(3-((3S,4aS,8aR)-8a-methyl-6-oxo-4a,5,6,8a-tetrahydrobenzo[e][1,2,4]trioxin-3-yl)propyl)isoindoline-1,3-dione
  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.