7-Chloro-3,3-dimethyl-1-(2-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one | 210419-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-Chloro-3,3-dimethyl-1-(2-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one
• 英文别名: 7-chloro-3,3-dimethyl-1-(2-methylbenzoyl)-2H-quinolin-4-one
• CAS: 210419-90-2
• 化学式: C₁₉H₁₈ClNO₂
• 分子量: 327.81
• InChiKey: DGJAFNVJYSSVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Chloro-3,3-dimethyl-1-(2-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到7-Chloro-3,3-dimethyl-1-(2-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one oxime
  参考文献：
  名称：

  Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives

  摘要：

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80061-5
• 作为产物：
  描述：

  7-chloro-2,3-dihydro-1-(2-methyl-benzoyl)-4(1H)-quinolinone 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以10%的产率得到7-Chloro-3-methyl-1-(2-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one
  参考文献：
  名称：

  Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives

  摘要：

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80061-5

文献信息

• Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives
  作者：Kazumi Nishijima、Tomoaki Shinkawa、Yoshiaki Yamashita、Naofumi Sato、Hidemitsu Nishida、Kazuo Kato、Yoshiaki Onuki、Masahiro Mizota、Kikuo Ohtomo、Soutarou Miyano

  DOI：10.1016/s0223-5234(98)80061-5

  日期：1998.4

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.