methyl 2-(5,5,8a-trimethyl-5,6,7,8-tetrahydro-1(8aH)-benzopyranyl)acetate | 68380-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2-(5,5,8a-trimethyl-5,6,7,8-tetrahydro-1(8aH)-benzopyranyl)acetate
• 英文别名: methyl 2-(5,5,8a-trimethyl-7,8-dihydro-6H-chromen-2-yl)acetate
• CAS: 68380-16-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: IMQAPVGJODHWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(5,5,8a-trimethyl-5,6,7,8-tetrahydro-1(8aH)-benzopyranyl)acetate 在 polymer-bound Rose Bengal 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以52%的产率得到methyl 2-(2,4a-epidioxy-4a,5,6,7,8,8a-hexahydro-5,5,8a-trimethyl-2H-1-benzopyran-2-yl)acetate
  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：

  methyl-5-(2',6',6'-trimethylcyclohex-1'-enyl)-3-ketop-4-pentenoate 在 三乙胺 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 1.0h， 以100%的产率得到methyl 2-(5,5,8a-trimethyl-5,6,7,8-tetrahydro-1(8aH)-benzopyranyl)acetate
  参考文献：
  名称：

  Lewis acid and photochemically mediated cyclization of olefinic .beta.-keto esters

  摘要：

  DOI：

  10.1021/jo00211a030

文献信息

• Lewis acid and photochemically mediated cyclization of olefinic .beta.-keto esters
  作者：James D. White、Richard W. Skeean、Gary L. Trammell

  DOI：10.1021/jo00211a030

  日期：1985.5
• 1,2,4-Trioxanes as potential antimalarial agents
  作者：John A. Kepler、Abraham Philip、Y. W. Lee、Matthew C. Morey、F. Ivy Carroll

  DOI：10.1021/jm00399a004

  日期：1988.4

  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.