cyclopent-2-en[18O]one | 23403-84-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: cyclopent-2-en[18O]one
• 英文别名: cyclopent-2-en[¹⁸O]one
• CAS: 23403-84-1
• 化学式: C₅H₆O
• 分子量: 84.1026
• InChiKey: BZKFMUIJRXWWQK-ZQBYOMGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cyclopent-2-en[18O]one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+/-)-18O-Cyclopent-2-en-1-ol
  参考文献：
  名称：

  Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

  摘要：

  H-2-Labelled and O-18-labelled cyclopentenyl esters (+/-)-4 and (+/-)-5 are used as probes for memory effects in Pd-catalysed allylic alkylation. H-2-Labelled alkylation product 6 arising from stereospecific Pd-catalysed reaction of (+/-)-4 was analysed by a novel C-13 NMR method involving H-2-isotope shifts and paramagnetic diastereotopic shifts. When catalysts bearing the Trost modular ligand (R,R)-3 were employed, variable memory effects were observed with the slower reacting chirality mismatched (R)-4 substrate-catalyst pairing. The memory effect is dependent on nucleofuge steric bulk and not pK(a). Attack by [LiCH(CO2CH3)(2)] occurs with reversed site selectivity but (R)-4 remains the mismatched substrate. Mismatched ionisation leading to a Pd-pi-allyl in which (R,R)-3 acts as a monophosphine ligand may explain the memory effect.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2539::aid-chem2539>3.0.co;2-1
• 作为产物：
  描述：

  2-环戊烯-1-酮缩乙醛 在 草酸 、 重氧水 作用下， 生成 cyclopent-2-en[18O]one
  参考文献：
  名称：

  Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

  摘要：

  H-2-Labelled and O-18-labelled cyclopentenyl esters (+/-)-4 and (+/-)-5 are used as probes for memory effects in Pd-catalysed allylic alkylation. H-2-Labelled alkylation product 6 arising from stereospecific Pd-catalysed reaction of (+/-)-4 was analysed by a novel C-13 NMR method involving H-2-isotope shifts and paramagnetic diastereotopic shifts. When catalysts bearing the Trost modular ligand (R,R)-3 were employed, variable memory effects were observed with the slower reacting chirality mismatched (R)-4 substrate-catalyst pairing. The memory effect is dependent on nucleofuge steric bulk and not pK(a). Attack by [LiCH(CO2CH3)(2)] occurs with reversed site selectivity but (R)-4 remains the mismatched substrate. Mismatched ionisation leading to a Pd-pi-allyl in which (R,R)-3 acts as a monophosphine ligand may explain the memory effect.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2539::aid-chem2539>3.0.co;2-1