cis-2,6-dipropylpiperidine | 157056-66-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: cis-2,6-dipropylpiperidine
• 英文别名: cis-2,3-dipropylpiperidine；(2S,6R)-2,6-dipropylpiperidine
• CAS: 157056-66-1
• 化学式: C₁₁H₂₃N
• 分子量: 169.31
• InChiKey: QCLNURWGDDEBFA-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-2,6-dipropylpiperidine 、 碘甲烷 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以99%的产率得到N,N-dimethyl-cis-2,3-dipropylpiperidinium iodide
  参考文献：
  名称：

  Reductivetrans-2,6-diallylation of pyridines with allylboranes. Synthesis oftrans- andcis-2,6-diallyl-1,2,5,6-tetrahydropyridines and their deuterated derivatives

  摘要：

  The reductive trans-2,6-diallylation of pyridines with triallyl- and allyI(dialkyl)boranes has been discovered. Heating (40-100 degrees C) of pyridine, deuteropyridine, or 3-bromopyridine complexes with triallylborane in the presence of alcohols (ROH or CH3OD), water, or Et(2)NH results in the respective trans-2,6-diallyl-1,2,5,6-tetrahydropyridines (2, 3, 22, or 25) In 20-97% yields. A preparative method for the isomerization of trans-2,6-diallyl compounds 2 and 25 into the respective cis-isomers 4 and 28 by heating them with triallyl- or allyl(dialkyl)boranes (125-150 degrees C) has been suggested. The hydrogenation of trans- or cis-2,6-diallyl-1,2,5,6-tetrahydropyridines gave trans- or cis-2,6-dipropylpiperidines, respectively. The cis- and trans-configurations of compounds 2 and 4 were established by analyzing the NMR spectra of N-benzyl (7 and 13) and N,N-dimethyl (6 and 14) derivatives of piperidine derivatives 5 and 8. A possible mechanism for the reductive diallylation of pyridines has been discussed.

  DOI：

  10.1007/bf00699842
• 作为产物：
  描述：

  cis-2,6-diallyl-1,2,5,6-tetrahydropyridine 在 镍 氢气 作用下， 以 溶剂黄146 为溶剂， 95.0~100.0 ℃ 、9.63 MPa 条件下， 反应 10.0h， 以90%的产率得到cis-2,6-dipropylpiperidine
  参考文献：
  名称：

  Reductivetrans-2,6-diallylation of pyridines with allylboranes. Synthesis oftrans- andcis-2,6-diallyl-1,2,5,6-tetrahydropyridines and their deuterated derivatives

  摘要：

  The reductive trans-2,6-diallylation of pyridines with triallyl- and allyI(dialkyl)boranes has been discovered. Heating (40-100 degrees C) of pyridine, deuteropyridine, or 3-bromopyridine complexes with triallylborane in the presence of alcohols (ROH or CH3OD), water, or Et(2)NH results in the respective trans-2,6-diallyl-1,2,5,6-tetrahydropyridines (2, 3, 22, or 25) In 20-97% yields. A preparative method for the isomerization of trans-2,6-diallyl compounds 2 and 25 into the respective cis-isomers 4 and 28 by heating them with triallyl- or allyl(dialkyl)boranes (125-150 degrees C) has been suggested. The hydrogenation of trans- or cis-2,6-diallyl-1,2,5,6-tetrahydropyridines gave trans- or cis-2,6-dipropylpiperidines, respectively. The cis- and trans-configurations of compounds 2 and 4 were established by analyzing the NMR spectra of N-benzyl (7 and 13) and N,N-dimethyl (6 and 14) derivatives of piperidine derivatives 5 and 8. A possible mechanism for the reductive diallylation of pyridines has been discussed.

  DOI：

  10.1007/bf00699842