4-(2-cyclopropylethynyl)-5,6,7-trifluoro-4-(trifluoromethyl)-1H-3,1-benzoxazin-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: 4-(2-cyclopropylethynyl)-5,6,7-trifluoro-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• 化学式: C₁₄H₇F₆NO₂
• 分子量: 335.205
• InChiKey: GGIUCMQQSUHIKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4,5-三氟苯胺 在 盐酸 、 正丁基锂 、 TEA 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 4-(2-cyclopropylethynyl)-5,6,7-trifluoro-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of analogs of Efavirenz (SUSTIVATM) as HIV-1 reverse transcriptase inhibitors

  摘要：

  Efavirenz (SUSTIVA(TM)) is a potent non-nucleoside reverse transcriptase inhibitor. Due to the observation of breakthrough mutations of the reverse transcriptase enzyme during Efavirenz therapy, we sought to develop an optimized second generation series. To that end, SAR of the substituents on the aromatic ring was undertaken and the results are summarized here. The 5,6-difluoro (4f) and the 6-methoxy (4m) substituted benzoxazinones were determined to be equipotent, and as a result such substitution patterns will be incorporated in second generation scaffolds. (C) 1999 DuPont Pharmaceuticals. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00486-2

文献信息

• Synthesis and evaluation of analogs of Efavirenz (SUSTIVATM) as HIV-1 reverse transcriptase inhibitors
  作者：Mona Patel、Soo S. Ko、Robert J. McHugh、Jay A. Markwalder、Anurag S. Srivastava、Beverly C. Cordova、Ronald M. Klabe、Susan Erickson-Viitanen、George L. Trainor、Steven.P. Seitz

  DOI：10.1016/s0960-894x(99)00486-2

  日期：1999.10

  Efavirenz (SUSTIVA(TM)) is a potent non-nucleoside reverse transcriptase inhibitor. Due to the observation of breakthrough mutations of the reverse transcriptase enzyme during Efavirenz therapy, we sought to develop an optimized second generation series. To that end, SAR of the substituents on the aromatic ring was undertaken and the results are summarized here. The 5,6-difluoro (4f) and the 6-methoxy (4m) substituted benzoxazinones were determined to be equipotent, and as a result such substitution patterns will be incorporated in second generation scaffolds. (C) 1999 DuPont Pharmaceuticals. Published by Elsevier Science Ltd. All rights reserved.