7-((1S)-1-phenylethyl)-7-azabicyclo[2.2.1]heptane-1-carbonitrile | 882182-36-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-((1S)-1-phenylethyl)-7-azabicyclo[2.2.1]heptane-1-carbonitrile
• 英文别名: 7-[(1S)-1-phenylethyl]-7-azabicyclo[2.2.1]heptane-1-carbonitrile
• CAS: 882182-36-7
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: GZAQBDIYDGLXNC-GRTSSRMGSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  343.2±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-((1S)-1-phenylethyl)-7-azabicyclo[2.2.1]heptane-1-carbonitrile 在 palladium on activated charcoal 盐酸 、 氢气 、 吡啶 作用下， 以 甲醇 为溶剂， 35.0 ℃ 、3.55 MPa 条件下， 以39%的产率得到7-氮杂双环[2.2.1]庚烷-1-羧酸
  参考文献：
  名称：

  立体选择性合成2,4-甲基脯氨酸的同系物

  摘要：

  报道了新颖的刚性双环脯氨酸类似物2-氮杂双环[2.2.1]庚烷-1-羧酸和6-氮杂双环[3.2.1]辛烷-5-羧酸的立体选择性合成。由相应的2-环烯-1-酮以五个步骤进行合成。改进了已知的2，4-甲基脯氨酸的方法。这三个氨基酸构成了构象受限的脯氨酸类似物的文库，其可用于拟肽和肽模型的设计。

  DOI：

  10.1016/j.tetasy.2005.12.009
• 作为产物：
  描述：

  2-methyl-2-((1-phenylethyl)amino)propane-nitrile 、 4-氯环己酮 在 (S)-(-)-α-methylbenzylamine hydrochloride 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以23%的产率得到7-((1S)-1-phenylethyl)-7-azabicyclo[2.2.1]heptane-1-carbonitrile
  参考文献：
  名称：

  An approach to 2-cyanopyrrolidines bearing a chiral auxiliary

  摘要：

  The reaction of 2-methyl-2-(1-phenylethyl)amino)propanenitrile with different gamma-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic gamma-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.008

文献信息

• Stereoselective synthesis of 2,4-methanoproline homologues
  作者：Oleksandr O. Grygorenko、Oleksiy S. Artamonov、Gennady V. Palamarchuk、Roman I. Zubatyuk、Oleg V. Shishkin、Igor V. Komarov

  DOI：10.1016/j.tetasy.2005.12.009

  日期：2006.1

  The stereoselective synthesis of 2-azabicyclo[2.2.1]heptane-1-carboxylic acid and 6-azabicyclo[3.2.1]octane-5-carboxylic acid, novel rigid bicyclic proline analogues, is reported. The synthesis was performed in five steps from the corresponding 2-cycloalken-1-ones. A known approach to 2,4-methanoproline is improved. The three amino acids constitute a library of conformationally constrained proline

  报道了新颖的刚性双环脯氨酸类似物2-氮杂双环[2.2.1]庚烷-1-羧酸和6-氮杂双环[3.2.1]辛烷-5-羧酸的立体选择性合成。由相应的2-环烯-1-酮以五个步骤进行合成。改进了已知的2，4-甲基脯氨酸的方法。这三个氨基酸构成了构象受限的脯氨酸类似物的文库，其可用于拟肽和肽模型的设计。
• An approach to 2-cyanopyrrolidines bearing a chiral auxiliary
  作者：Oleksandr O. Grygorenko、Nataliya A. Kopylova、Pavel K. Mikhailiuk、Anja Meißner、Igor V. Komarov

  DOI：10.1016/j.tetasy.2007.01.008

  日期：2007.2

  The reaction of 2-methyl-2-(1-phenylethyl)amino)propanenitrile with different gamma-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic gamma-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed. (c) 2007 Elsevier Ltd. All rights reserved.