(2R)-2-phenyl-2-((1S,5S)-7-phenyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl)ethanol | 181872-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (2R)-2-phenyl-2-((1S,5S)-7-phenyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl)ethanol
• 英文别名: (2R)-2-phenyl-2-[(1S,5S)-7-phenyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl]ethanol
• CAS: 181872-19-5
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: DSYIGQVGZASUGI-GBESFXJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-phenyl-2-((1S,5S)-7-phenyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl)ethanol 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以75%的产率得到(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
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 、 phenylmagnesium bromide 以 乙醚 为溶剂， 反应 18.0h， 以50%的产率得到(2R)-2-phenyl-2-((1S,5S)-7-phenyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl)ethanol
  参考文献：
  名称：

  氨基腈-恶唑烷与格氏试剂的反应中的取代和立体化学作用

  摘要：

  A study of the reaction of phenyl magnesium bromide with various N-(cyanomethyl)oxazolidines showed that product formation (essentially 3-imidazolines and 2-aminomorpholines) is highly sensitive to the substitution pattern and stereochemistry, and appears to involve initial complexation of the Grignard reagent to ring-oxygen. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00980-6

文献信息

• Practical Asymmetric Synthesis of 1,2-Diamines in the 3-Aminoazepane Series
  作者：S. Cutri、M. Bonin、L. Micouin、H.-P. Husson、A. Chiaroni

  DOI：10.1021/jo026711s

  日期：2003.4.1

  A simple and versatile method for the enantio- and diastereoselective synthesis of mono- or disubstituted 3-aminoazepanes is described. The key step involves a highly regio- and diastereoselective tandem ring-enlargement/alkylation or reduction process. This novel synthetic route provides enantiomerically pure constrained diamines interesting as scaffolds for medicinal chemistry.

  描述了一种简单和通用的方法，用于对映和非对映选择性合成单或双取代的3-氨基氮杂环丁烷。关键步骤涉及高度区域和非对映选择性的串联环扩大/烷基化或还原过程。这种新颖的合成途径提供了对映体纯的约束二胺，可用作药物化学的支架。
• Diastereoselective synthesis of 2-aryl-3-aminoazepanes via a novel ring-enlargement process
  作者：Sabrina Cutri、Martine Bonin、Laurent Micouin、Olivier Froelich、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(99)02256-x

  日期：2000.2

  Syntheses of optically pure 2-aryl-3-aminoazepanes derived from 2-cyano 6-oxazolopiperidine are described. The key step involves a one-pot reduction and ring-enlargement process occurring in a highly regio- and stereoselective way.

  描述了衍生自2-氰基6-恶唑并哌啶的光学纯的2-芳基-3-氨基氮杂环庚烷的合成。关键步骤涉及以高度区域选择性和立体选择性的方式进行的一锅还原和环扩大过程。
• Substitution and stereochemical effects in the reactions of combined aminonitrile-oxazolidines with a Grignard reagent
  作者：Marc Le Bail、Joëlle Pérard、David J. Aitken、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(99)00980-6

  日期：1999.7

  A study of the reaction of phenyl magnesium bromide with various N-(cyanomethyl)oxazolidines showed that product formation (essentially 3-imidazolines and 2-aminomorpholines) is highly sensitive to the substitution pattern and stereochemistry, and appears to involve initial complexation of the Grignard reagent to ring-oxygen. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• 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).