benzyl 5-hydroxy-3,3-dimethyl-piperidine-1-carboxylate | 1241922-20-2

• 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: benzyl 5-hydroxy-3,3-dimethyl-piperidine-1-carboxylate
• 英文别名: 5,5-dimethyl-1-carbobenzyloxypiperidin-3-ol；Benzyl 5-hydroxy-3,3-dimethylpiperidine-1-carboxylate
• CAS: 1241922-20-2
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: YVWDDNLLIHJZPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 2,2-dimethylpent-4-enylcarbamate 在 palladium(II) trifluoroacetate 、 水 、 N-氟代双苯磺酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42%的产率得到benzyl 5-hydroxy-3,3-dimethyl-piperidine-1-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxyamination of Alkenes with Use ofN-Fluorobenzenesulfonimide as Oxidant

  摘要：

  A Pd-catalyzed alkoxyamination of protected aminoalkenes promoted by N-fluorobenzenesulfonimide is described. This mild transformation allows the direct formation of ethers from carbon-carbon double bonds. An unusual switch from exo to endo selectivity in polar solvents was discovered, allowing the selective formation of either regioisomer by careful choice of reaction conditions.

  DOI：

  10.1021/jo101171g

文献信息

• Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes
  作者：Teresa de Haro、Cristina Nevado

  DOI：10.1002/anie.201005763

  日期：2011.1.24

  AuI/AuIII catalytic cycles can trigger three highly regioselective alkene difunctionalization processes that involve the formation of C(sp3)O, C(sp3)N, and C(sp3)C(sp2) bonds. The reaction can proceed by reductive elimination on the oxidized gold center with complete retention of the configuration or through two subsequent nucleophilic substitution reactions via an aziridine intermediate.

  的Au我/ Au的III 催化循环可以触发涉及C的形成三个高度区域选择性的烯烃difunctionalization过程（SP 3） O，C（SP 3） N，和C（SP 3） C（SP 2）键。该反应可通过在构型完全保留的情况下在氧化的金中心上进行还原性消除或通过氮丙啶中间体进行的两个后续亲核取代反应来进行。
• Palladium-Catalyzed Alkoxyamination of Alkenes with Use of<i>N</i>-Fluorobenzenesulfonimide as Oxidant
  作者：Dmitry V. Liskin、Paul A. Sibbald、Carolyn F. Rosewall、Forrest E. Michael

  DOI：10.1021/jo101171g

  日期：2010.9.17

  A Pd-catalyzed alkoxyamination of protected aminoalkenes promoted by N-fluorobenzenesulfonimide is described. This mild transformation allows the direct formation of ethers from carbon-carbon double bonds. An unusual switch from exo to endo selectivity in polar solvents was discovered, allowing the selective formation of either regioisomer by careful choice of reaction conditions.