(2S,4R)-4-methyl-2-propan-2-ylpyrrolidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,4R)-4-methyl-2-propan-2-ylpyrrolidine
• 化学式: C₈H₁₇N
• 分子量: 127.23
• InChiKey: NPOFEKDXRFTVQK-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-methyl-2-propan-2-ylpyrrolidine 、 氯甲酸苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (2S,4R)-2-isopropyl-4-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles

  摘要：

  The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated alpha-amino nitriles derived from enantiopure alpha-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to > 98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.

  DOI：

  10.1055/s-0031-1291046
• 作为产物：
  描述：

  (S)-2-(benzyl(2-methylhex-5-en-3-yl)amino)acetonitrile 在 正丁基锂 、 20 % Pd(OH)2/C 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -80.0~20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (2S,4R)-4-methyl-2-propan-2-ylpyrrolidine
  参考文献：
  名称：

  Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles

  摘要：

  The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated alpha-amino nitriles derived from enantiopure alpha-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to > 98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.

  DOI：

  10.1055/s-0031-1291046

文献信息

• 3-CYCLOALKYLAMINOPYRROLIDINE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTORS
  申请人：Xue Chu-Biao

  公开号：US20140155377A1

  公开（公告）日：2014-06-05

  The present invention relates to 3-cycloalkylaminopyrrolidine derivatives of the formula I: (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Y and Z are as defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of chemokine receptors and more specifically as modulators of the CCR2 and/or CCR5 receptor. The compounds and compositions of the invention may bind to chemokine receptors, e.g., the CCR2 and/or CCR5 chemokine receptors, and are useful for treating diseases associated with chemokine, e.g., CCR2 and/or CCR5, activity, such as atherosclerosis, restenosis, lupus, organ transplant rejection and rheumatoid arthritis.

  本发明涉及式I的3-环烷基氨基吡咯烷衍生物（其中R1，R2，R3，R4，R5，R6，R7，Y和Z如本文所定义），其作为趋化因子受体活性调节剂。特别地，这些化合物可作为趋化因子受体的调节剂，更具体地作为CCR2和/或CCR5受体的调节剂。本发明的化合物和组合物可以与趋化因子受体结合，例如CCR2和/或CCR5趋化因子受体，并可用于治疗与趋化因子，例如CCR2和/或CCR5活性相关的疾病，例如动脉粥样硬化、再狭窄、狼疮、器官移植排斥反应和类风湿性关节炎。
• Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles
  作者：Fabrice Chemla、Franck Ferreira、Alejandro Perez-Luna、Sabrina Ouizem

  DOI：10.1055/s-0031-1291046

  日期：2012.6

  The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated alpha-amino nitriles derived from enantiopure alpha-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to > 98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.