2-(3-Chlorophenyl)-3-hydroxy-3,4-dihydroisoquinolin-1-one | 220327-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(3-Chlorophenyl)-3-hydroxy-3,4-dihydroisoquinolin-1-one
• CAS: 220327-64-0
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: QMVBYGSDGYEKHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-Chlorophenyl)-3-hydroxy-3,4-dihydroisoquinolin-1-one 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 2-[2-(3-Chlorophenyl)-1-oxo-3,4-dihydroisoquinolin-3-yl]acetic acid
  参考文献：
  名称：

  Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives

  摘要：

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80028-2
• 作为产物：
  描述：

  2-(3-氯苯基)-4H-异喹啉-1,3-二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到2-(3-Chlorophenyl)-3-hydroxy-3,4-dihydroisoquinolin-1-one
  参考文献：
  名称：

  Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives

  摘要：

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80028-2

文献信息

• Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives
  作者：Kazumi Nishijima、Tomoaki Shinkawa、Manabu Ito、Hidemitsu Nishida、Ichirou Yamamoto、Yoshiaki Onuki、Hitoshi Inaba、Soutarou Miyano

  DOI：10.1016/s0223-5234(99)80028-2

  日期：1998.10

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.