8-chloro-3-(4-ethylphenyl)-10,11-dihydro-4,10-methanopyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acid | 1457989-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-chloro-3-(4-ethylphenyl)-10,11-dihydro-4,10-methanopyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acid
• 英文别名: 8-chloro-3-(4-ethylphenyl)-10,11-dihydro-4,10-methanopyrazolo[4,3-c][1,5]benzoxazocine-4(1H)-carboxylic acid；4-chloro-11-(4-ethylphenyl)-8-oxa-12,13,15-triazatetracyclo[7.6.1.02,7.010,14]hexadeca-2(7),3,5,10,13-pentaene-9-carboxylic acid
• CAS: 1457989-86-4
• 化学式: C₂₁H₁₈ClN₃O₃
• 分子量: 395.845
• InChiKey: SYHHSIOTAWLVRP-UHFFFAOYSA-N

物化性质

• 沸点：
  682.5±55.0 °C(predicted)
• 密度：
  1.434±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₁₈H₁₆ClN₃O 、 丙酮酸 在 溶剂黄146 作用下， 反应 1.5h， 生成 8-chloro-3-(4-ethylphenyl)-10,11-dihydro-4,10-methanopyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acid
  参考文献：
  名称：

  Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products

  摘要：

  Three-component reactions of 5-aminopyrazoles and salicylic aldehydes with pyruvic acids were studied. The method of tuning of the selectivity of the heterocyclizations allowing to change its direction by variation of the reaction parameters was worked out. The treatment involving pyruvic acid can be selectively directed to the formation to either 3-aryl-10,11-dihydro-4,10-methano-pyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acids or 3,6-diarylpyrazolo[3,4-b]pyridine-4-carboxylic acids, while the reaction involving arylpyruvic acid leads only to 7-hydroxy-2,5,6-triaryl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-7-carboxylic acids. Antimicrobial activity of the compounds obtained was also studied: Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) were found sensitive to the substances tested, however, only in the highest concentration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.055

文献信息

• Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products
  作者：Maryna V. Murlykina、Yana I. Sakhno、Sergey M. Desenko、Iryna S. Konovalova、Oleg V. Shishkin、Dmytro A. Sysoiev、Maryna N. Kornet、Valentin A. Chebanov

  DOI：10.1016/j.tet.2013.08.055

  日期：2013.11

  Three-component reactions of 5-aminopyrazoles and salicylic aldehydes with pyruvic acids were studied. The method of tuning of the selectivity of the heterocyclizations allowing to change its direction by variation of the reaction parameters was worked out. The treatment involving pyruvic acid can be selectively directed to the formation to either 3-aryl-10,11-dihydro-4,10-methano-pyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acids or 3,6-diarylpyrazolo[3,4-b]pyridine-4-carboxylic acids, while the reaction involving arylpyruvic acid leads only to 7-hydroxy-2,5,6-triaryl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-7-carboxylic acids. Antimicrobial activity of the compounds obtained was also studied: Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) were found sensitive to the substances tested, however, only in the highest concentration. (C) 2013 Elsevier Ltd. All rights reserved.