4-(4-Fluoro-benzyl)-2-(2-hydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one | 660390-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-(4-Fluoro-benzyl)-2-(2-hydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one
• CAS: 660390-91-0
• 化学式: C₁₇H₁₆FNO₃
• 分子量: 301.317
• InChiKey: IBHSGXWZSALXAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-benzyl)-2-(2-hydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one 在 sodium hydroxide 、 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 苯 为溶剂， 生成 (2-{2-[4-(4-Fluoro-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid
  参考文献：
  名称：

  Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions

  摘要：

  A series of benzoxazinones was synthesized as PPARgamma agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 muM. The potency was further confirmed through a PPAR-Ga14 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00401-3
• 作为产物：
  描述：

  3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪 在 咪唑 、 甲烷磺酸 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-Fluoro-benzyl)-2-(2-hydroxy-ethyl)-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions

  摘要：

  A series of benzoxazinones was synthesized as PPARgamma agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 muM. The potency was further confirmed through a PPAR-Ga14 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00401-3