6-bromo-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-benzo[b][1,4]oxazine | 1277192-89-8

• 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: 6-bromo-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-benzo[b][1,4]oxazine
• 英文别名: 6-bromo-5,7,8-trimethyl-2-phenyl-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 1277192-89-8
• 化学式: C₁₇H₁₈BrNO
• 分子量: 332.24
• InChiKey: VDPHGTKUQHAGHN-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  437.3±45.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-噻吩硼酸 、 6-bromo-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-benzo[b][1,4]oxazine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.08h， 以85%的产率得到3,4-dihydro-5,7,8-trimethyl-2-phenyl-6-(thiophen-2-yl)-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：

  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

文献信息

• 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
  作者：Eftychia N. Koini、Nicolaos Avlonitis、Erica S. Martins-Duarte、Wanderley de Souza、Rossiane C. Vommaro、Theodora Calogeropoulou

  DOI：10.1016/j.tet.2012.10.009

  日期：2012.12

  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.