2-[2-(4-Methoxyphenyl)ethynyl]cyclopent-2-en-1-one | 1234889-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[2-(4-Methoxyphenyl)ethynyl]cyclopent-2-en-1-one
• 英文别名: 2-[2-(4-methoxyphenyl)ethynyl]cyclopent-2-en-1-one
• CAS: 1234889-24-7
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: FGZCHNFRXOXYBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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， 20.0~110.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 methyl 4-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-5,6-dihydro-4H-cyclopenta[b]furan-3-carboxylate
  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 、 4-乙炔基苯甲醚 生成 2-[2-(4-Methoxyphenyl)ethynyl]cyclopent-2-en-1-one
  参考文献：
  名称：

  A convenient synthetic route to furan esters and lactones by palladium-catalyzed carboalkoxylation or cyclocarbonylation of hydroxyl-substituted 3-iodofurans

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.04.108

文献信息

• Addition of Primary Amines to 2-(1-Alkynyl)-2-cycloalken-1-ones
  作者：Aurelija Urbanaitė、Lukas Šteinys、Algirdas Brukštus、Inga Čikotienė

  DOI：10.1002/ejoc.201700119

  日期：2017.3.27

  The regio‐ and stereoselective nucleophilic addition of primary aliphatic amines to 2‐(1‐alkynyl)‐2‐cycloalken‐1‐ones proceeds through double‐bond migration. In particular, (Z)‐β‐enaminones having cycloalkene rings can be prepared through a mild and atom‐economical route.

  伯脂族胺向2-（1-炔基）-2-环烯烃-1-酮的区域和立体选择性亲核加成通过双键迁移进行。特别是，可以通过温和且经济的原子路线制备具有环烯环的（Z）-β-烯酮。
• 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.
• 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.
• 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.