5,6,7,8-tetrahydro-2-(2-hydroxypropyl)-5,5,8a-trimethyl-8aH-1-benzopyran | 113087-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5,6,7,8-tetrahydro-2-(2-hydroxypropyl)-5,5,8a-trimethyl-8aH-1-benzopyran
• 英文别名: 1-(5,5,8a-trimethyl-7,8-dihydro-6H-chromen-2-yl)propan-2-ol
• CAS: 113087-82-4
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: GHKIIFWRHMGCAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-2-(2-hydroxypropyl)-5,5,8a-trimethyl-8aH-1-benzopyran 在 吡啶 、 polymer-bound Rose Bengal 、 氧气 、 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 40.0h， 生成 2,4a-epidioxy-3,4,4a,5,6,7,8,8a-octahydro-2-<2-(benzoyloxy)propyl>-5,5,8a-trimethyl-2H-1-benzopyran
  参考文献：
  名称：

  1,2,4-Trioxanes as potential antimalarial agents

  摘要：

  A number of 1,2,4-trioxanes were prepared and tested for antimalarial activity in search of a simplified analogue of the naturally occurring antimalarial qinghaosu. The compounds were assayed in an in vitro system for antimalarial activity against chloroquine-susceptible and chloroquine-resistant strains of Plasmodium falciparum. The most active compounds were methyl 2-(2,4a-epidioxy-4a,5,6,7,8,8a-hexahydro-5,5,8a-trimethyl-2H-1-benzop yra n-2-yl) acetate (3b), which showed IC20's of 96 and 39 ng/mL, respectively, and 2,4a-epidioxy-3,4,4a,5,6,7,8,8a-octahydro-2-[2-(benzoyloxy)propyl]-5,5,8 a- trimethyl-2H-1-benzopyran (12), which showed IC50's of 24 and 99 ng/mL, respectively. For comparison, qinghaosu exhibits an IC50 of 1 ng/mL for both strains.

  DOI：

  10.1021/jm00399a004
• 作为产物：
  描述：

  2-hydroxy-4-oxo-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-5-hexene 在 三乙胺 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 4.0h， 以71%的产率得到5,6,7,8-tetrahydro-2-(2-hydroxypropyl)-5,5,8a-trimethyl-8aH-1-benzopyran
  参考文献：
  名称：

  1,2,4-Trioxanes as potential antimalarial agents

  摘要：

  A number of 1,2,4-trioxanes were prepared and tested for antimalarial activity in search of a simplified analogue of the naturally occurring antimalarial qinghaosu. The compounds were assayed in an in vitro system for antimalarial activity against chloroquine-susceptible and chloroquine-resistant strains of Plasmodium falciparum. The most active compounds were methyl 2-(2,4a-epidioxy-4a,5,6,7,8,8a-hexahydro-5,5,8a-trimethyl-2H-1-benzop yra n-2-yl) acetate (3b), which showed IC20's of 96 and 39 ng/mL, respectively, and 2,4a-epidioxy-3,4,4a,5,6,7,8,8a-octahydro-2-[2-(benzoyloxy)propyl]-5,5,8 a- trimethyl-2H-1-benzopyran (12), which showed IC50's of 24 and 99 ng/mL, respectively. For comparison, qinghaosu exhibits an IC50 of 1 ng/mL for both strains.

  DOI：

  10.1021/jm00399a004