2-phenyl-6-bromo-5,7,8-trimethyl-1,4-benzoxazinone | 1277192-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-phenyl-6-bromo-5,7,8-trimethyl-1,4-benzoxazinone
• CAS: 1277192-87-6
• 化学式: C₁₇H₁₆BrNO₂
• 分子量: 346.224
• InChiKey: KRCDSXLABQJRPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-6-bromo-5,7,8-trimethyl-1,4-benzoxazinone 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到6-bromo-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-benzo[b][1,4]oxazine
  参考文献：
  名称：

  Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki–Miyaura cross coupling and biological evaluation

  摘要：

  An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling protocol effected in a mixture of DME/water (2:1) enables the reaction of sterically hindered and electron rich 6-chloro or 6-bromo-1,4-benzoxazines(ones) with a variety of aryl, vinyl or alkylboronic acids. Coupling is effected with catalyst loading of 5 mol % using sealed-vessel microwave processing. The resulting compounds exhibit potent activity against Toxoplasma gondii tachyzoite proliferation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.009
• 作为产物：
  描述：

  5,7,8-trimethyl-2-phenyl-2H-1,4-benzoxazin-3(4H)-one 在 氢溴酸 、 双氧水 、 溶剂黄146 作用下， 以 Petroleum ether 为溶剂， 反应 1.0h， 以65%的产率得到2-phenyl-6-bromo-5,7,8-trimethyl-1,4-benzoxazinone
  参考文献：
  名称：

  Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki–Miyaura cross coupling and biological evaluation

  摘要：

  An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling protocol effected in a mixture of DME/water (2:1) enables the reaction of sterically hindered and electron rich 6-chloro or 6-bromo-1,4-benzoxazines(ones) with a variety of aryl, vinyl or alkylboronic acids. Coupling is effected with catalyst loading of 5 mol % using sealed-vessel microwave processing. The resulting compounds exhibit potent activity against Toxoplasma gondii tachyzoite proliferation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.009