2-hydroxyethyl 4-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-3-carboxylate | 1234889-41-8

• 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-hydroxyethyl 4-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-3-carboxylate
• CAS: 1234889-41-8
• 化学式: C₁₉H₂₂O₇
• 分子量: 362.379
• InChiKey: PYHVVJUHDYEYDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[2-(4-Methoxyphenyl)ethynyl]cyclopent-2-en-1-one 在 碘 、 palladium diacetate 、 碳酸氢钠 、 三乙胺 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 2-hydroxyethyl 4-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-3-carboxylate
  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

• 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.
• 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.