2-(phenoxymethyl)-2,3-dihydrobenzo[b][1,4]dioxine

• 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: 2-(phenoxymethyl)-2,3-dihydrobenzo[b][1,4]dioxine
• 英文别名: 3-(Phenoxymethyl)-2,3-dihydro-1,4-benzodioxine
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: XDABSQKNBMWVAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘苯酚 、 苯基缩水甘油醚 在 copper(I) oxide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以71%的产率得到2-(phenoxymethyl)-2,3-dihydrobenzo[b][1,4]dioxine
  参考文献：
  名称：

  Cu₂O-Catalyzed Tandem Ring-Opening/Coupling Cyclization Process for the Synthesis of 2,3-Dihydro-1,4-benzodioxins

  摘要：

  2, 3-Dihydro-1,4-benzodioxins can be prepared in a tandem one-pot procedure by reaction of o-iodophenols with epoxides catalyzed by Cu2O/1,10-phenanthroline/Cs2CO3 system. The reaction is suggested to occur via a novel ring-opening/coupling mechanism, giving moderate to good yields. Moreover, both aryl and aliphatic epoxides are tolerated under these conditions.

  DOI：

  10.1021/ol801444p

文献信息

• Copper-catalyzed tandem process: an efficient approach to 2-substituted-1,4-benzodioxanes
  作者：Yunyun Liu、Weiliang Bao

  DOI：10.1039/c003691a

  日期：——

  An efficient method for the preparation of various 2-substituted-1,4-benzodioxanes by CuBr-catalyzed tandem reactions of 2-((o-iodophenoxy)methyl)oxiranes with phenols has been developed. The reaction involves the ring-opening process of 2-((2-iodophenoxy)methyl)oxirane followed by an intramolecular C–O cross coupling cyclization.

  一种高效的方法已被开发，用于通过CuBr催化的串联反应，将2-((o-碘苯氧基)methyl)环氧烷与酚类化合物制备多种2-取代-1,4-苯并二恶烷。该反应涉及2-((2-碘苯氧基)methyl)环氧烷的开环过程，随后进行分子内C–O交叉耦合环化反应。
• Cu₂O-Catalyzed Tandem Ring-Opening/Coupling Cyclization Process for the Synthesis of 2,3-Dihydro-1,4-benzodioxins
  作者：Weiliang Bao、Yunyun Liu、Xin Lv、Weixing Qian

  DOI：10.1021/ol801444p

  日期：2008.9.1

  2, 3-Dihydro-1,4-benzodioxins can be prepared in a tandem one-pot procedure by reaction of o-iodophenols with epoxides catalyzed by Cu2O/1,10-phenanthroline/Cs2CO3 system. The reaction is suggested to occur via a novel ring-opening/coupling mechanism, giving moderate to good yields. Moreover, both aryl and aliphatic epoxides are tolerated under these conditions.