4-chloro-1-(2-cyanoethyl)-2-phenylindole | 220327-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-chloro-1-(2-cyanoethyl)-2-phenylindole
• 英文别名: 3-(4-Chloro-2-phenylindol-1-yl)propanenitrile
• CAS: 220327-46-8
• 化学式: C₁₇H₁₃ClN₂
• 分子量: 280.757
• InChiKey: TUXWOHBWCVGQPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-1-(2-cyanoethyl)-2-phenylindole 在 硫酸 、 phosphorus pentoxide 、 potassium carbonate 、 hydroxylamine-O-sulfonic acid 作用下， 以 xylene 为溶剂， 反应 1.5h， 生成 9-chloro-4,5-dihydro-2-phenyl-6H-pyrrolo(3,2,1-ij)quinolin-6-one 6-oxime-O-sulfonic acid potassium salt
  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-氯-6-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 氯化亚砜 、 过氧化氢苯甲酰 、 硫酸 、 苄基三甲基氢氧化铵 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 30.17h， 生成 4-chloro-1-(2-cyanoethyl)-2-phenylindole
  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