Methyl 3-(5-bromo-2-fluorophenyl)-2-cyanoprop-2-enoate | 848908-19-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl 3-(5-bromo-2-fluorophenyl)-2-cyanoprop-2-enoate
• CAS: 848908-19-0
• 化学式: C₁₁H₇BrFNO₂
• 分子量: 284.084
• InChiKey: FYJJERQGSKZJKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丙二烯基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷 、 Methyl 3-(5-bromo-2-fluorophenyl)-2-cyanoprop-2-enoate 在 cis-dichlorobis(benzonitrile)palladium(II) 、 sodium t-butanolate 、 叔丁醇 、 (5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yl)dimethylamine 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到methyl 2-(5-bromo-2-fluorophenyl)-1-cyanocyclopent-3-enecarboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis

  摘要：

  Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.

  DOI：

  10.1021/ol2019423

文献信息

• Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis
  作者：Benjamin L. Kohn、Elizabeth R. Jarvo

  DOI：10.1021/ol2019423

  日期：2011.9.16

  Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.