tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate | 158414-43-8

• 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: tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate
• 英文别名: tert-butyl (1R,2R)-2-[benzyl-[(1R)-1-phenylethyl]amino]cyclopentane-1-carboxylate
• CAS: 158414-43-8
• 化学式: C₂₅H₃₃NO₂
• 分子量: 379.543
• InChiKey: INHCOTUHYJWTGR-UEVCKROQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate 在 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 三丁基膦 、 甲酸铵 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 4.0h， 生成 ((1S,2R)-2-Amino-cyclopentylmethyl)-(4-ethoxy-quinolin-2-yl)-amine
  参考文献：
  名称：

  Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity

  摘要：

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00093-3
• 作为产物：
  描述：

  tert-butyl cyclopentanecarboxylate 在 2,6-二叔丁基苯酚 、 碘 、 双(三甲基硅烷基)氨基钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 叔丁醇 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 195.0h， 生成 tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate
  参考文献：
  名称：

  （–）-（1 R，2 S）-顺喷他星及其相关顺式和反式-2-氨基环戊烷和环己烷-1-羧酸的不对称合成

  摘要：

  抗真菌抗生素（–）-（1 R，2 S）-2-氨基环戊烷-1-羧酸（顺喷塔星）8及其环己烷同系物14是通过高立体选择性共轭加成手性锂N-苄基-N-制备的。 α-甲基苄基酰胺5。还通过顺式-β-氨基酯缀合物加成产物的选择性差向异构化制备了相应的反式-β-氨基酸10和16。

  DOI：

  10.1039/p19940001411

文献信息

• Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity
  作者：Richard L. Jarvest、John M. Berge、Pamela Brown、Catherine S.V. Houge-Frydrych、Peter J. O'Hanlon、David J. McNair、Andrew J. Pope、Stephen Rittenhouse

  DOI：10.1016/s0960-894x(03)00093-3

  日期：2003.4

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of (–)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids
  作者：Stephen G. Davies、Osamu Ichihara、Isabelle Lenoir、Iain A. S. Walters

  DOI：10.1039/p19940001411

  日期：——

  The antifungal antibiotic (–)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin)8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide 5. The corresponding trans-β-amino acids 10 and 16 were also prepared via the selective epimerization of the cis-β-amino ester conjugate addition products

  抗真菌抗生素（–）-（1 R，2 S）-2-氨基环戊烷-1-羧酸（顺喷塔星）8及其环己烷同系物14是通过高立体选择性共轭加成手性锂N-苄基-N-制备的。 α-甲基苄基酰胺5。还通过顺式-β-氨基酯缀合物加成产物的选择性差向异构化制备了相应的反式-β-氨基酸10和16。