(3R,5S)-5-Cyclopropylethynyl-7-fluoro-3-methyl-5-trifluoromethyl-1,5-dihydro-benzo[e][1,4]oxazepin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (3R,5S)-5-Cyclopropylethynyl-7-fluoro-3-methyl-5-trifluoromethyl-1,5-dihydro-benzo[e][1,4]oxazepin-2-one
• 英文别名: (3R,5S)-5-(2-cyclopropylethynyl)-7-fluoro-3-methyl-5-(trifluoromethyl)-1H-4,1-benzoxazepin-2-one
• 化学式: C₁₆H₁₃F₄NO₂
• 分子量: 327.278
• InChiKey: CXFITMZADXBGRR-PSLIRLAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2-Amino-5-fluoro-phenyl)-4-cyclopropyl-1,1,1-trifluoro-but-3-yn-2-ol 在 吡啶 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3R,5S)-5-Cyclopropylethynyl-7-fluoro-3-methyl-5-trifluoromethyl-1,5-dihydro-benzo[e][1,4]oxazepin-2-one
  参考文献：
  名称：

  4,1-Benzoxazepinone analogues of efavirenz (Sustiva™) as HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of 4,1-benzoxazepinone analogues of efavirenz (Sustiva(TM)) as potent NNRTIs has been discovered. The cis-3-alkylbenzoxazepinones are more potent then the trans isomers and can be synthesized preferentially by a novel stereoselective cyclization. The best compounds are potent orally bioavailable inhibitors of both wild-type HIV-1 and its clinically relevant K103N mutant virus, but are highly protein-bound in human plasma. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00239-6

文献信息

• 4,1-Benzoxazepinone analogues of efavirenz (Sustiva™) as HIV-1 reverse transcriptase inhibitors
  作者：Anthony J. Cocuzza、Dennis R. Chidester、Beverly C. Cordova、Ronald M. Klabe、Susan Jeffrey、Sharon Diamond、Carolyn A. Weigelt、Soo S. Ko、Lee T. Bacheler、Susan K. Erickson-Viitanen、James D. Rodgers

  DOI：10.1016/s0960-894x(01)00239-6

  日期：2001.6

  A series of 4,1-benzoxazepinone analogues of efavirenz (Sustiva(TM)) as potent NNRTIs has been discovered. The cis-3-alkylbenzoxazepinones are more potent then the trans isomers and can be synthesized preferentially by a novel stereoselective cyclization. The best compounds are potent orally bioavailable inhibitors of both wild-type HIV-1 and its clinically relevant K103N mutant virus, but are highly protein-bound in human plasma. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.