ethyl 5-hydroxy-6,10-dioxo-9-azatetracyclo[7.7.1.02,8.012,17]heptadeca-1(17),2,4,7,11,13,15-heptaene-11-carboxylate | 1210941-28-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: ethyl 5-hydroxy-6,10-dioxo-9-azatetracyclo[7.7.1.02,8.012,17]heptadeca-1(17),2,4,7,11,13,15-heptaene-11-carboxylate
• CAS: 1210941-28-8
• 化学式: C₁₉H₁₃NO₅
• 分子量: 335.316
• InChiKey: ZIWUNIOQERBKBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-hydroxy-11-azacyclohept[a]azulen-3(3H)-one 、 丙二酸二乙酯 在 乙酸酐 作用下， 反应 1.5h， 以21%的产率得到ethyl 5-hydroxy-6,10-dioxo-9-azatetracyclo[7.7.1.02,8.012,17]heptadeca-1(17),2,4,7,11,13,15-heptaene-11-carboxylate
  参考文献：
  名称：

  Synthesis and Some Reactions of 11-Azacyclohept[a]azulen-3(3H)-ones and Evaluation of Their Cytotoxic Activity against HeLa S3 Cells

  摘要：

  Aldol condensation of 2,3-diformyl-1-azaazulene with acetone, methoxyacetone, and benzylacetone in aq. NaOH solution gave corresponding 11-azacyclohept[a]azulen-3(3H)-one (2a), 2-methoxy-derivative (2b) and 2-benzyl-derivative (2d) in good yields. Hydrolysis of 2b using hot HBr gave 2-hydroxy-11-azacyclohept[a]azulen-3(3H)-one (2f). Acetylation of 2f gave 2-acetoxy-11-azacyclohept[a]azulen-3(3H)-one (2g). Reaction of the compounds (2a, 2b, 2f) with diethyl malonate in Ac2O under heating gave 1,9(11bH)-11b-azaazuleno[1,2,3-cd]azulenedione derivatives (4a, 4b, 4f). Compounds (2b, 2f) showed weak cytotoxic activity against He La S3 cells.

  DOI：

  10.3987/com-09-s(s)39

文献信息

• Synthesis and Some Reactions of 11-Azacyclohept[a]azulen-3(3H)-ones and Evaluation of Their Cytotoxic Activity against HeLa S3 Cells
  作者：Noritaka Abe、Tomoyuki Ariyoshi、Kengo Yoshinaga、Kazuya Koizumi、Hiroyuki Fujii、Takeo Konakahara、Reiko Ikeda

  DOI：10.3987/com-09-s(s)39

  日期：——

  Aldol condensation of 2,3-diformyl-1-azaazulene with acetone, methoxyacetone, and benzylacetone in aq. NaOH solution gave corresponding 11-azacyclohept[a]azulen-3(3H)-one (2a), 2-methoxy-derivative (2b) and 2-benzyl-derivative (2d) in good yields. Hydrolysis of 2b using hot HBr gave 2-hydroxy-11-azacyclohept[a]azulen-3(3H)-one (2f). Acetylation of 2f gave 2-acetoxy-11-azacyclohept[a]azulen-3(3H)-one (2g). Reaction of the compounds (2a, 2b, 2f) with diethyl malonate in Ac2O under heating gave 1,9(11bH)-11b-azaazuleno[1,2,3-cd]azulenedione derivatives (4a, 4b, 4f). Compounds (2b, 2f) showed weak cytotoxic activity against He La S3 cells.