5,7-difluoro-2,2-dimethyl-2H-quinoline-1-carboxylic acid t-butyl ester | 1181824-21-4

• 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: 5,7-difluoro-2,2-dimethyl-2H-quinoline-1-carboxylic acid t-butyl ester
• 英文别名: Tert-butyl 5,7-difluoro-2,2-dimethylquinoline-1-carboxylate；tert-butyl 5,7-difluoro-2,2-dimethylquinoline-1-carboxylate
• CAS: 1181824-21-4
• 化学式: C₁₆H₁₉F₂NO₂
• 分子量: 295.329
• InChiKey: QCBFMCHBUNXMRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-difluoro-2,2-dimethyl-2H-quinoline-1-carboxylic acid t-butyl ester 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 硼烷四氢呋喃络合物 、 双氧水 、 sodium carbonate 、 pyridinium chlorochromate 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.0h， 生成 (E)-(±)-5,7-Difluoro-6-(indol-7-yl)-2,3-dihydro-2,2-dimethyl-1H-quinolin-4-one
  参考文献：
  名称：

  Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation

  摘要：

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.104
• 作为产物：
  描述：

  1,1-二甲基丙-2-炔基乙酸酯 在 正丁基锂 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 15.0h， 生成 5,7-difluoro-2,2-dimethyl-2H-quinoline-1-carboxylic acid t-butyl ester
  参考文献：
  名称：

  Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation

  摘要：

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.104

文献信息

• [EN] STEROID HORMONE RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS MODULATEURS DES RÉCEPTEURS DE L'HORMONE STÉROÏDIENNE ET PROCÉDÉS
  申请人：LIGAND PHARM INC

  公开号：WO2009103007A3

  公开（公告）日：2009-11-19
• Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation
  作者：Andrew R. Hudson、Robert I. Higuchi、Steven L. Roach、Lino J. Valdez、Mark E. Adams、Angie Vassar、Deepa Rungta、Peter M. Syka、Dale E. Mais、Keith B. Marschke、Lin Zhi

  DOI：10.1016/j.bmcl.2011.01.104

  日期：2011.3

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.