5-bromo-6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxin | 148330-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-bromo-6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxin
• 英文别名: 5-Bromo-6-(oxan-2-yloxy)-2,3-dihydro-1,4-benzodioxine
• CAS: 148330-24-9
• 化学式: C₁₃H₁₅BrO₄
• 分子量: 315.164
• InChiKey: CJIQSQKXEOQJOK-UHFFFAOYSA-N

物化性质

• 沸点：
  395.5±42.0 °C(predicted)
• 密度：
  1.486±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxin 在 甲醇 、 草酸 作用下， 以97%的产率得到5-bromo-6-hydroxy-2,3-dihydro-1,4-benzodioxin
  参考文献：
  名称：

  Convenient synthesis of 5-substituted-6-methoxy or 6-hydroxy-2,3-dihydro-1,4-benzodioxins via lithiated intermediates

  摘要：

  The 6-methoxy and 6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxins can be lithiated at the 5-position to give intermediate lithio derivatives which react with various electrophiles to afford, after hydrolysis, 5-substituted-6-methoxy and 6-hydroxy-2,3-dihydro-1,4-benzodioxins.

  DOI：

  10.1016/s0040-4020(01)90194-2
• 作为产物：
  描述：

  6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxin 在 正丁基锂 、 1,1,2,2-四氟-1,2-二溴乙烷 作用下， 生成 5-bromo-6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxin
  参考文献：
  名称：

  Convenient synthesis of 5-substituted-6-methoxy or 6-hydroxy-2,3-dihydro-1,4-benzodioxins via lithiated intermediates

  摘要：

  The 6-methoxy and 6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxins can be lithiated at the 5-position to give intermediate lithio derivatives which react with various electrophiles to afford, after hydrolysis, 5-substituted-6-methoxy and 6-hydroxy-2,3-dihydro-1,4-benzodioxins.

  DOI：

  10.1016/s0040-4020(01)90194-2

文献信息

• Convenient synthesis of 5-substituted-6-methoxy or 6-hydroxy-2,3-dihydro-1,4-benzodioxins via lithiated intermediates
  作者：Thierry Besson、Mohamed Hretani、Gérard Coudert、Gérald Guillaumet

  DOI：10.1016/s0040-4020(01)90194-2

  日期：1993.2

  The 6-methoxy and 6-tetrahydropyranyloxy-2,3-dihydro-1,4-benzodioxins can be lithiated at the 5-position to give intermediate lithio derivatives which react with various electrophiles to afford, after hydrolysis, 5-substituted-6-methoxy and 6-hydroxy-2,3-dihydro-1,4-benzodioxins.
• Synthesis of a benzodioxinic analog of 8-methoxypsoralen
  作者：Thierry Besson、Nicolas Ruiz、Gérard Coudert、Gérald Guillaumet

  DOI：10.1016/0040-4020(95)00058-g

  日期：1995.3

  A synthesis of a benzodioxinic analog of 8-methoxypsoralen (8-MOP), in 12 steps from the commercially available 6-acetyl-2,3-dihydro-1,4-benzodioxin, is described.