1,3-dibromo-5-methoxy-2-(methoxymethoxy)benzene | 1402694-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-dibromo-5-methoxy-2-(methoxymethoxy)benzene
• 英文别名: 1,3-Dibromo-5-methoxy-2-(methoxymethoxy)benzene
• CAS: 1402694-51-2
• 化学式: C₉H₁₀Br₂O₃
• 分子量: 325.985
• InChiKey: PUGVLJVZHCHEHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-methoxy-2-(methoxymethoxy)benzene 在 四(三苯基膦)钯 、 正丁基锂 、 copper(I) bromide dimethylsulfide complex 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 2',3-digeranyl-5,3',6'-trimethoxy-2-(methoxymethoxy)biphenyl
  参考文献：
  名称：

  Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A

  摘要：

  A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6 pi-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.

  DOI：

  10.1021/jo301738u
• 作为产物：
  描述：

  4-甲氧基苯酚 在 1,8-diazabicyclo[5.4.0]-undecen-7-ene 、 benzyltrimethylazanium tribroman-2-uide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.5h， 生成 1,3-dibromo-5-methoxy-2-(methoxymethoxy)benzene
  参考文献：
  名称：

  Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A

  摘要：

  A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6 pi-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.

  DOI：

  10.1021/jo301738u

文献信息

• Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A
  作者：Anna Carbone、Catherine L. Lucas、Christopher J. Moody

  DOI：10.1021/jo301738u

  日期：2012.10.19

  A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6 pi-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.