(2S,3S,6S)-6-allyl-3-methyl-2-(2-phenylethyl)piperidine | 1290057-81-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,3S,6S)-6-allyl-3-methyl-2-(2-phenylethyl)piperidine
• 英文别名: (2S,3S,6S)-3-methyl-2-(2-phenylethyl)-6-prop-2-enylpiperidine
• CAS: 1290057-81-6
• 化学式: C₁₇H₂₅N
• 分子量: 243.392
• InChiKey: ULUOZOADIZPXAU-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S,2S,5aS,10bR)-2-ethyl-1-(2-phenylethyl)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridine 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S,6S)-6-allyl-3-methyl-2-(2-phenylethyl)piperidine
  参考文献：
  名称：

  Cyclohydrocarbonylation-Based Strategy toward Poly- Substituted Piperidines

  摘要：

  Convenient accesses to enantiomerically pure 2-, 2,3-, 2,6-, 2,3,6-substituted piperidines and 1,4-substituted indolizine are described. At first, indium-mediated aminoallylation and -crotylation of aldehydes with (R)-phenylglycinol or (1R,2S)-1-amino-2-indanol gave homoallylamines with high stereocontrol. Then, these products, submitted to a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation, afforded perhydrooxazolo [3,2-a]piridines whose oxazolidines are opened with nucleophiles. Finally, the removal of the chiral auxiliaries delivered the enantiomerically pure piperidines.

  DOI：

  10.1021/ol200557r

文献信息

• Cyclohydrocarbonylation-Based Strategy toward Poly- Substituted Piperidines
  作者：Giada Arena、Nicolas Zill、Jessica Salvadori、Nicolas Girard、André Mann、Maurizio Taddei

  DOI：10.1021/ol200557r

  日期：2011.5.6

  Convenient accesses to enantiomerically pure 2-, 2,3-, 2,6-, 2,3,6-substituted piperidines and 1,4-substituted indolizine are described. At first, indium-mediated aminoallylation and -crotylation of aldehydes with (R)-phenylglycinol or (1R,2S)-1-amino-2-indanol gave homoallylamines with high stereocontrol. Then, these products, submitted to a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation, afforded perhydrooxazolo [3,2-a]piridines whose oxazolidines are opened with nucleophiles. Finally, the removal of the chiral auxiliaries delivered the enantiomerically pure piperidines.