ethyl 4,4-dicyano-5-(furan-2-yl)cyclopent-1-ene-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: ethyl 4,4-dicyano-5-(furan-2-yl)cyclopent-1-ene-1-carboxylate
• 英文别名: Ethyl 4,4-dicyano-5-(furan-2-yl)cyclopentene-1-carboxylate
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: OPJUJUTZJSNTOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 (2-呋喃亚甲基)丙二腈 在 (S)-tBu-binepine 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 ethyl 4,4-dicyano-5-(furan-2-yl)cyclopent-1-ene-1-carboxylate 、 ethyl 4,4-dicyano-5-(furan-2-yl)cyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Studies on the asymmetric, phosphine-promoted [3+2] annulations of allenic esters with 2-aryl-1,1-dicyanoalkenes

  摘要：

  The first enantioselective variant of the phosphine-promoted [3+2] cycloaddition reaction between allenoates and 2-aryl-1,1-dicyanoethylenes has been developed. The use of (S)-t-butyl-Binepine as the chiral organocatalyst allows the synthesis of functionalized cyclopentenes with both aryl and heteroaryl substituents on the stereogenic carbon, in high yields and ees of up to 95%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.014

文献信息

• Phosphine-catalyzed one-pot synthesis of cyclopentenes from electron-deficient allene, malononitrile and aromatic aldehydes
  作者：Xiyan Lu、Zheng Lu、Xumu Zhang

  DOI：10.1016/j.tet.2005.09.100

  日期：2006.1

  A three component reaction of aryl aldehydes and malononitrile with ethyl 2,3-butadienoate catalyzed by triphenylphosphine has been developed. The reaction furnishes highly functionalized cyclopentenes in moderate to good yields in a one-pot process.

  已开发了由三苯膦催化的芳基醛和丙二腈与2,3-丁二烯酸乙酯的三组分反应。该反应通过一锅法以中等到良好的产率提供高度官能化的环戊烯。
• Studies on the asymmetric, phosphine-promoted [3+2] annulations of allenic esters with 2-aryl-1,1-dicyanoalkenes
  作者：Marie Schuler、Arnaud Voituriez、Angela Marinetti

  DOI：10.1016/j.tetasy.2010.04.014

  日期：2010.6

  The first enantioselective variant of the phosphine-promoted [3+2] cycloaddition reaction between allenoates and 2-aryl-1,1-dicyanoethylenes has been developed. The use of (S)-t-butyl-Binepine as the chiral organocatalyst allows the synthesis of functionalized cyclopentenes with both aryl and heteroaryl substituents on the stereogenic carbon, in high yields and ees of up to 95%. (C) 2010 Elsevier Ltd. All rights reserved.