(1R,4aS,5aS,10bR)-1-(2-furyl)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridine | 1290057-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,4aS,5aS,10bR)-1-(2-furyl)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridine
• 英文别名: (1R,3R,7S,9S)-3-(furan-2-yl)-8-oxa-2-azatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-triene
• CAS: 1290057-67-8
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: XAPXJIGHNYGSQM-LAVFITLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4aS,5aS,10bR)-1-(2-furyl)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridine 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， -78.0 ℃ 、1.01 MPa 条件下， 生成 (2R,6R)-2-(2-furyl)-6-methylpiperidine
  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：

  (1R,2S)-1-氨基-2-茚醇 在 dicarbonylacetylacetonatorhodium(I) 、 氢气 、 sodium sulfate 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、827.39 kPa 条件下， 反应 27.0h， 生成 (1R,4aS,5aS,10bR)-1-(2-furyl)-2,3,4,4a,6,10b-hexahydro-1H,5aH-indeno[1',2':4,5][1,3]oxazolo[3,2-a]pyridine
  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.