2-[[2-[4-(Dimethylamino)phenyl]-3-iodo-4,5,6,7-tetrahydro-1-benzofuran-4-yl]oxy]ethanol | 1283730-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-[[2-[4-(Dimethylamino)phenyl]-3-iodo-4,5,6,7-tetrahydro-1-benzofuran-4-yl]oxy]ethanol
• CAS: 1283730-98-2
• 化学式: C₁₈H₂₂INO₃
• 分子量: 427.282
• InChiKey: GSECURXXVJTRKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[2-[4-(Dimethylamino)phenyl]-3-iodo-4,5,6,7-tetrahydro-1-benzofuran-4-yl]oxy]ethanol 、 4-氨基甲酰苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以53%的产率得到4-(2-(4-(dimethylamino)phenyl)-4-(2-hydroxyethoxy)-4,5,6,7-tetrahydrobenzofuran-3-yl)benzamide
  参考文献：
  名称：

  Solution-Phase Synthesis of a Highly Substituted Furan Library

  摘要：

  A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

  DOI：

  10.1021/co300040q
• 作为产物：
  描述：

  1-(4-喹啉基)甲胺 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 碘 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[[2-[4-(Dimethylamino)phenyl]-3-iodo-4,5,6,7-tetrahydro-1-benzofuran-4-yl]oxy]ethanol
  参考文献：
  名称：

  Solution-Phase Synthesis of a Highly Substituted Furan Library

  摘要：

  A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

  DOI：

  10.1021/co300040q

文献信息

• Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-Iodofurans
  作者：Chul-Hee Cho、Richard C. Larock

  DOI：10.1021/co100088q

  日期：2011.5.9

  Highly substituted lactone- and ester-containing furans have been prepared by the efficient palladium-catalyzed intramolecular cyclocarbonylation or intermolecular carboalkoxylation, respectively, of hydroxyl-containing 3-iodofurans, readily prepared by the iodocyclization of 2(1-alkynyl)-2-alken-1-ones in the presence of various diols.