1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-6,7-dimethoxyisochroman | 1454883-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-6,7-dimethoxyisochroman
• CAS: 1454883-66-9
• 化学式: C₁₉H₁₉BrO₅
• 分子量: 407.261
• InChiKey: WENOJMCIDNOJBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-6,7-dimethoxyisochroman 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以93%的产率得到1,2-dimethoxy-4,5,6a,7-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]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：

  methyl 2-(6-bromobenzo[d][1,3]dioxol-5-yl)acetate 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 calcium chloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.5h， 生成 1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-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