2-((2-(4-(dimethylamino)phenyl)-3-iodo-5,6-dihydro-4H-cyclopenta[b]furan-4-yl)oxy)ethan-1-ol | 1283731-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-((2-(4-(dimethylamino)phenyl)-3-iodo-5,6-dihydro-4H-cyclopenta[b]furan-4-yl)oxy)ethan-1-ol
• CAS: 1283731-06-5
• 化学式: C₁₇H₂₀INO₃
• 分子量: 413.255
• InChiKey: ZVQHNCWXJVUVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  45.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-((2-(4-(dimethylamino)phenyl)-3-iodo-5,6-dihydro-4H-cyclopenta[b]furan-4-yl)oxy)ethan-1-ol 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 以61%的产率得到4-(4-(dimethylamino)phenyl)-2,7,8,9a-tetrahydro-1H,5H-3,6,9-trioxacycloocta[cd]pentalen-5-one
  参考文献：
  名称：

  Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-Iodofurans

  摘要：

  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.

  DOI：

  10.1021/co100088q
• 作为产物：
  描述：

  2-碘-2-环戊烯-1-酮 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-5,6-dihydro-4H-cyclopenta[b]furan-4-yl)oxy)ethan-1-ol
  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