3,4-dihydro-5,7,8-trimethyl-2-phenyl-6-(thiophen-2-yl)-2H-benzo[b][1,4]oxazine | 1277193-55-1

• 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: 3,4-dihydro-5,7,8-trimethyl-2-phenyl-6-(thiophen-2-yl)-2H-benzo[b][1,4]oxazine
• 英文别名: 5,7,8-trimethyl-2-phenyl-6-thiophen-2-yl-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 1277193-55-1
• 化学式: C₂₁H₂₁NOS
• 分子量: 335.47
• InChiKey: PVUXKBXSGYWSPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,7,8-trimethyl-2-phenyl-2H-1,4-benzoxazin-3(4H)-one 在 四(三苯基膦)钯 、 dimethyl sulfide borane 、 氢溴酸 、 双氧水 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 Petroleum ether 为溶剂， 反应 13.08h， 生成 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

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.