2-[[3-iodo-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-4-yl]oxy]ethanol | 1234889-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-[[3-iodo-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-4-yl]oxy]ethanol
• CAS: 1234889-29-2
• 化学式: C₁₆H₁₇IO₄
• 分子量: 400.213
• InChiKey: LQRGHXBZFRHPOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-[[3-iodo-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-4-yl]oxy]ethanol 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63%的产率得到2-(4-Methoxyphenyl)-3,8,11-trioxatricyclo[5.5.1.04,13]trideca-1,4(13)-dien-12-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：

  4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 碳酸氢钠 、 二异丙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[[3-iodo-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-4-yl]oxy]ethanol
  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

文献信息

• Solution-Phase Synthesis of a Highly Substituted Furan Library
  作者：Chul-Hee Cho、Feng Shi、Dai-Il Jung、Benjamin Neuenswander、Gerald H. Lushington、Richard C. Larock

  DOI：10.1021/co300040q

  日期：2012.7.9

  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.
• A convenient synthetic route to furan esters and lactones by palladium-catalyzed carboalkoxylation or cyclocarbonylation of hydroxyl-substituted 3-iodofurans
  作者：Chul-Hee Cho、Richard C. Larock

  DOI：10.1016/j.tetlet.2010.04.108

  日期：2010.6

  An effective palladium-catalyzed protocol for the intermolecular carboalkoxylation or intramolecular cyclocarbonylation of hydroxyl-substituted 3-iodofurans under carbon monoxide pressure has been developed. The 3-iodofurans are readily prepared by iodocyclization of 2-(1-alkynyl)-2-alken-1-ones in the presence of various diols. (C) 2010 Elsevier Ltd. All rights reserved.