1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxyisochroman | 1454883-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxyisochroman
• 英文别名: 1-[(2-bromo-4,5-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isochromene
• CAS: 1454883-62-5
• 化学式: C₂₀H₂₃BrO₅
• 分子量: 423.304
• InChiKey: SNFONJSFUSBKDA-UHFFFAOYSA-N

物化性质

• 沸点：
  511.0±50.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxyisochroman 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 140.0 ℃ 、1.38 MPa 条件下， 反应 0.17h， 以89%的产率得到1,2,9,10-tetramethoxy-4,5,6a,7-tetrahydrodibenzo[de,g]chromene
  参考文献：
  名称：

  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

  摘要：

  Oxa-Pictet Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g] chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.095
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸甲酯 在 sodium tetrahydroborate 、 对甲苯磺酸 、 calcium chloride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 34.0h， 生成 1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxyisochroman
  参考文献：
  名称：

  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

  摘要：

  Oxa-Pictet Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g] chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.095