(2R)-2-[(2S)-2-[amino(diphenyl)methyl]piperidin-1-yl]-2-phenylethanol | 181872-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-[(2S)-2-[amino(diphenyl)methyl]piperidin-1-yl]-2-phenylethanol
• CAS: 181872-32-2
• 化学式: C₂₆H₃₀N₂O
• 分子量: 386.537
• InChiKey: KSEVTBZQBSQXBV-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(2S)-2-[amino(diphenyl)methyl]piperidin-1-yl]-2-phenylethanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(4R,9aS)-1,1,4-triphenyloctahydro-2H-pyrido[1,2-a]pyrazine
  参考文献：
  名称：

  Asymmetric Synthesis of Octahydro-2H-pyrido[1,2-a]pyrazines

  摘要：

  DOI：

  10.3987/com-99-8544
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 sodium tetrahydroborate 、 lithium bromide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (2R)-2-[(2S)-2-[amino(diphenyl)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

文献信息

• Asymmetric Synthesis of Octahydro-2H-pyrido[1,2-a]pyrazines
  作者：Jean-Charles Quirion、Olivier Froelich、Françoise Cossart、Martine Bonin、Henri-Philippe Husson

  DOI：10.3987/com-99-8544

  日期：——
• 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).