dimethyl 2-ethyl-3-phenylcyclopent-2-ene-1,1-dicarboxylate | 1379038-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-ethyl-3-phenylcyclopent-2-ene-1,1-dicarboxylate
• 英文别名: Dimethyl 2-ethyl-3-phenylcyclopent-2-ene-1,1-dicarboxylate
• CAS: 1379038-06-8
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: BDQUNHPCWFSDAK-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯苯 、 2-hex-3-ynyl-malonic acid dimethyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 、 dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphine 、 sodium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 以81%的产率得到dimethyl 2-ethyl-3-phenylcyclopent-2-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m

文献信息

• Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-<i>Endo-Dig</i> Cyclization
  作者：Daishi Fujino、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1021/ol301257m

  日期：2012.6.1

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.