(E)-5-[1-(toluene-4-sulfonyl)aziridin-2-yl]pent-2-enoic acid butyl ester

• 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: (E)-5-[1-(toluene-4-sulfonyl)aziridin-2-yl]pent-2-enoic acid butyl ester
• 英文别名: butyl (E)-5-[1-(4-methylphenyl)sulfonylaziridin-2-yl]pent-2-enoate
• 化学式: C₁₈H₂₅NO₄S
• 分子量: 351.467
• InChiKey: URCKKIKQOXMXIY-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,5-已二烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.25h， 生成 (E)-5-[1-(toluene-4-sulfonyl)aziridin-2-yl]pent-2-enoic acid butyl ester
  参考文献：
  名称：

  Synthesis and Reactivity of Azapalladacyclobutanes

  摘要：

  N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd-2(dba)(3) and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo-[3.2.1] octanes. A deuterium-labeling experiment indicates that the oxidative addition proceeds via S(N)2-type attack of palladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn fashion. The azapalladabicyclo[3.2.1] octane complexes undergo oxidative palladium-carbon bond functionalization in the presence of copper(II) bromide.

  DOI：

  10.1021/ja0660756

文献信息

• Synthesis and Reactivity of Azapalladacyclobutanes
  作者：Joshua E. Ney、John P. Wolfe

  DOI：10.1021/ja0660756

  日期：2006.12.1

  N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd-2(dba)(3) and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo-[3.2.1] octanes. A deuterium-labeling experiment indicates that the oxidative addition proceeds via S(N)2-type attack of palladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn fashion. The azapalladabicyclo[3.2.1] octane complexes undergo oxidative palladium-carbon bond functionalization in the presence of copper(II) bromide.