(1S,4R,9aS)-1,4-diphenyl-4,6,7,8,9,9a-hexahydro-3H-pyrido[2,1-c][1,4]oxazin-1-amine | 181872-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1S,4R,9aS)-1,4-diphenyl-4,6,7,8,9,9a-hexahydro-3H-pyrido[2,1-c][1,4]oxazin-1-amine
• CAS: 181872-21-9
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: ZXQBELYKYOMRHG-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R,9aS)-1,4-diphenyl-4,6,7,8,9,9a-hexahydro-3H-pyrido[2,1-c][1,4]oxazin-1-amine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以94%的产率得到(2R)-2-{(2S)-2-[(R)-(1-aminophenyl)methyl]piperidin-1-yl}-2-phenylethanol
  参考文献：
  名称：

  Asymmetric Synthesis. 39.¹ Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine

  摘要：

  The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).

  DOI：

  10.1021/jo960910s
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 (1S,4R,9aS)-1,4-diphenyl-4,6,7,8,9,9a-hexahydro-3H-pyrido[2,1-c][1,4]oxazin-1-amine
  参考文献：
  名称：

  Asymmetric Synthesis. 39.¹ Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine

  摘要：

  The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).

  DOI：

  10.1021/jo960910s

文献信息

• Asymmetric Synthesis. 39.¹ Synthesis of 2-(1-Aminoalkyl)piperidines <i>via</i> 2-Cyano-6-phenyl Oxazolopiperidine
  作者：Olivier Froelich、Patrice Desos、Martine Bonin、Jean-Charles Quirion、Henri-Philippe Husson、Jieping Zhu

  DOI：10.1021/jo960910s

  日期：1996.1.1

  The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).