(3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridine | 88056-98-8

• 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: (3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridine
• 英文别名: (5S)-3-Phenyl-5-propylhexahydrooxazolo<3,2-a>pyridine；(3R,5S)-3-phenyl-5-propylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridine；(3R,5S)-3-phenyl-5-propyl-3,5,6,7,8,8a-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridine
• CAS: 88056-98-8
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: MMRHZVHXMBZJQT-KSCSMHSMSA-N

物化性质

• 沸点：
  347.3±30.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridine 在 palladium on carbon 、 氢气 作用下， 以76%的产率得到毒芹碱
  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
• 作为产物：
  描述：

  (+)-(3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以93%的产率得到(3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridine
  参考文献：
  名称：

  5-烷基-3-苯基-2,3,5,6,7,8-六氢-恶唑并[3,2 - a ]吡啶-4-碘化碘的受控还原：（-）-二氢吡啶和（ +）-吲哚唑烷167B

  摘要：

  （+）-（3 R，5 S）-5-甲基-和（+）-（3 R，5 S）-5- n-丙基-3-苯基-2,3,5,6的受控还原，7,8-六氢-恶唑并[3,2- a ]吡啶-4-基碘鎓碘化物1和2生成（3 R，5 S）-5-甲基-和（3 R，5 S）-5- n据报道，分别是-丙基-3-苯基-2,3,5,6,7,8-六氢-恶唑并[3,2- a ]吡啶3和4。另外，（-）-（2 R，6 S）-二氢吡啶和（+）-（2获得了分别从3和4开始的S，6S）-吲哚唑烷167B 。

  DOI：

  10.1016/j.tetasy.2004.09.030

文献信息

• Chiral 1,4-dihydropyridine equivalents: a new approach to the asymmetric synthesis of alkaloids. The enantiospecific synthesis of (+)- and (-)-coniine and dihydropinidine
  作者：Luc Guerrier、Jacques Royer、David S. Grierson、Henri Philippe Husson

  DOI：10.1021/ja00364a053

  日期：1983.12
• A New Approach to the Asymmetric Synthesis of Carbacephams
  作者：Jean-Francois Berrien、Marie-Annick Billion、Henri-Philippe Husson、Jacques Royer

  DOI：10.1021/jo00114a053

  日期：1995.5
• 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.
• Controlled reduction of 5-alkyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide: enantioselective synthesis of (−)-dihydropinidine and (+)-indolizidine 167B
  作者：Luis F. Roa、Dino Gnecco、Alberto Galindo、Joel L. Terán

  DOI：10.1016/j.tetasy.2004.09.030

  日期：2004.11

  reduction of (+)-(3R,5S)-5-methyl- and (+)-(3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 1 and 2 to generate (3R,5S)-5-methyl- and (3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridine 3 and 4, respectively, is reported. In addition, an enantioselective synthesis of (−)-(2R,6S)-dihydropinidine and (+)-(2S,6S)-indolizidine 167B starting from

  （+）-（3 R，5 S）-5-甲基-和（+）-（3 R，5 S）-5- n-丙基-3-苯基-2,3,5,6的受控还原，7,8-六氢-恶唑并[3,2- a ]吡啶-4-基碘鎓碘化物1和2生成（3 R，5 S）-5-甲基-和（3 R，5 S）-5- n据报道，分别是-丙基-3-苯基-2,3,5,6,7,8-六氢-恶唑并[3,2- a ]吡啶3和4。另外，（-）-（2 R，6 S）-二氢吡啶和（+）-（2获得了分别从3和4开始的S，6S）-吲哚唑烷167B 。