1-benzyloxy-2-oxopiperidine-3-carboxylic acid ethyl ester | 1284281-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyloxy-2-oxopiperidine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-oxo-1-phenylmethoxypiperidine-3-carboxylate；ethyl 2-oxo-1-phenylmethoxypiperidine-3-carboxylate
• CAS: 1284281-81-7
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: KWPCKTYHTDMQDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-2-oxopiperidine-3-carboxylic acid ethyl ester 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 生成 N,N-dimethyl 3-methyl-1-hydroxy-2-oxo-3-piperidinecarboxamide
  参考文献：
  名称：

  Combining Desferriferrioxamine B and 1‐Hydroxy‐2‐Piperidone ((PIPO)H) to Chelate Zirconium. Solution Structure of a Model Complex of the [⁸⁹Zr]Zr−DFOcyclo*−mAb Radioimmunoconjugate

  摘要：

  ⁸⁹Zr−immunoPET is a hot topic as ⁸⁹Zr cumulates the advantages of ⁶⁴Cu and ¹²⁴I without their drawbacks. We report the synthesis of a model ligand of a chiral bioconjugable tetrahydroxamic chelator combining the desferriferrioxamine B siderophore and 1‐hydroxy‐2‐piperidone ((PIPO)H), a chiral cyclic hydroxamic acid derivative, and the study by NMR spectroscopy of its zirconium complex. Nuclear Overhauser effect measurements (ROESY) indicated that the complex exists in the form of two diastereomers, in 77 : 23 ratio, resulting from the combination of the central chiralities at the 3‐C of the (PIPO)H component and at the Zr⁴⁺ cation. The 44 lowest energy structures out of more than 1000 configurations/conformations returned by calculations based on density functional theory were examined. Comparison of the ROESY data and the calculated interatomic H⋅⋅⋅H distances allowed us to select the most probable configuration and conformations of the major complex.

  DOI：

  10.1002/cplu.202400062
• 作为产物：
  描述：

  5-(N-benzyloxy(ethoxycarbonyl)amino)pentanoic acid ethyl ester 在 lithium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以80.8%的产率得到1-benzyloxy-2-oxopiperidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  环状异羟肟酸的新方法：N-苄氧基氨基甲酸酯与碳亲核试剂的分子内环化

  摘要：

  N-烷基-N-苄氧基氨基甲酸酯2与各种碳亲核试剂进行轻松的分子内环化，得到官能化的五元和六元受保护环状异羟肟酸3，收率良好至极好。该方法可以扩展到以中等产率制备七元环异羟肟酸。本研究中的砜中间体3可以被烷基化，而相应的膦酸酯已被证明可以进行 HWE 反应。α,β-不饱和合成子, 8 , 亚砜3m热消去制备, 与仲胺发生迈克尔加成。这种方法中，以制备多齿螯合剂的实用性已经通过双环状异羟肟酸的合成方法证实12，14，和15。

  DOI：

  10.1016/j.tet.2011.01.073

文献信息

• A new approach to cyclic hydroxamic acids: intramolecular cyclization of N-benzyloxy carbamates with carbon nucleophiles
  作者：Yuan Liu、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tet.2011.01.073

  日期：2011.3

  moderate yields. The sulfone intermediates 3 from this study can be alkylated while the corresponding phosphonates have been shown to undergo HWE reaction. The α,β-unsaturated synthon, 8, prepared by thermal elimination of sulfoxide 3m, undergoes Michael addition with secondary amines. The usefulness of this approach to prepare polydentate chelators has been demonstrated by the synthesis of bis cyclic hydroxamic

  N-烷基-N-苄氧基氨基甲酸酯2与各种碳亲核试剂进行轻松的分子内环化，得到官能化的五元和六元受保护环状异羟肟酸3，收率良好至极好。该方法可以扩展到以中等产率制备七元环异羟肟酸。本研究中的砜中间体3可以被烷基化，而相应的膦酸酯已被证明可以进行 HWE 反应。α,β-不饱和合成子, 8 , 亚砜3m热消去制备, 与仲胺发生迈克尔加成。这种方法中，以制备多齿螯合剂的实用性已经通过双环状异羟肟酸的合成方法证实12，14，和15。
• Combining Desferriferrioxamine B and 1‐Hydroxy‐2‐Piperidone ((PIPO)H) to Chelate Zirconium. Solution Structure of a Model Complex of the [⁸⁹Zr]Zr−DFOcyclo*−mAb Radioimmunoconjugate
  作者：Floriane Mangin、Osian Fonquernie、Pawel Jewula、Stéphane Brandès、Marie‐José Penouilh、Quentin Bonnin、Bruno Vincent、Enrique Espinosa、Emmanuel Aubert、Michel Meyer、Jean‐Claude Chambron

  DOI：10.1002/cplu.202400062

  日期：——

  ⁸⁹Zr−immunoPET is a hot topic as ⁸⁹Zr cumulates the advantages of ⁶⁴Cu and ¹²⁴I without their drawbacks. We report the synthesis of a model ligand of a chiral bioconjugable tetrahydroxamic chelator combining the desferriferrioxamine B siderophore and 1‐hydroxy‐2‐piperidone ((PIPO)H), a chiral cyclic hydroxamic acid derivative, and the study by NMR spectroscopy of its zirconium complex. Nuclear Overhauser effect measurements (ROESY) indicated that the complex exists in the form of two diastereomers, in 77 : 23 ratio, resulting from the combination of the central chiralities at the 3‐C of the (PIPO)H component and at the Zr⁴⁺ cation. The 44 lowest energy structures out of more than 1000 configurations/conformations returned by calculations based on density functional theory were examined. Comparison of the ROESY data and the calculated interatomic H⋅⋅⋅H distances allowed us to select the most probable configuration and conformations of the major complex.