(2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester | 178813-27-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester
• 英文别名: tert-butyl (2S,5R)-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate
• CAS: 178813-27-9
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: AEAFMWNKYCTVNI-BDAKNGLRSA-N

物化性质

• 沸点：
  316.8±32.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester 在 三丁基膦 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (2S)-cis-1-(2-acetylaminoacryloyl)-5-(2-phenylselenoethyl)proline tert-butyl ester
  参考文献：
  名称：

  Colombo, Lino; Giacomo, Marcello Di; Belvisi, Laura, Gazzetta Chimica Italiana, 1996, vol. 126, # 8, p. 543 - 554

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R-cis)-5-((1,1-Dimethylethoxy)carbonyl)-1-(phenylmethyl)-2-pyrrolidineacetic acid methyl ester 在 palladium dihydroxide 锂硼氢 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester
  参考文献：
  名称：

  立体选择性自由基环化反应合成7,5-稠合双环内酰胺

  摘要：

  通过涉及中间体2的自由基环化的途径，合成了1型的7,5-稠合双环内酰胺。在该反应中获得了高水平的立体选择。

  DOI：

  10.1016/s0040-4039(00)76732-3

文献信息

• Synthesis of 7,5-fused bicyclic lactams by stereoselective radical cyclization
  作者：Lino Colombo、Marcello Di Giacomo、Gianluca Papeo、Oliviero Carugo、Carlo Scolastico、Leonardo Manzoni

  DOI：10.1016/s0040-4039(00)76732-3

  日期：1994.6

  7,5-Fused bicyclic lactams of type 1 were synthesised by a route involving the radical cyclization of the intermediate 2. High level of stereoselection was obtained in this reaction.

  通过涉及中间体2的自由基环化的途径，合成了1型的7,5-稠合双环内酰胺。在该反应中获得了高水平的立体选择。
• Design and synthesis of conformationally constrained arginal thrombin inhibitors
  作者：Aldo Salimbeni、Fabio Paleari、Renato Canevotti、Marco Criscuoli、Marco Criscuoli、Annalisa Lippi、Mauro Angiolini、Laura Belvisi、Carlo Scolastico、Lino Colombo

  DOI：10.1016/s0960-894x(97)00403-4

  日期：1997.9

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.
• Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics
  作者：Lino Colombo、Marcello Di Giacomo、Gloria Brusotti、Nicola Sardone、Mauro Angiolini、Laura Belvisi、Sonia Maffioli、Leonardo Manzoni、Carlo Scolastico

  DOI：10.1016/s0040-4020(98)00207-5

  日期：1998.5

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.
• [EN] BICYCLIC LACTAM DERIVATIVES AS THROMBIN INHIBITORS<br/>[FR] DERIVES LACTAMES BICYCLIQUES UTILISES COMME INHIBITEURS DE THROMBINE
  申请人：A. MENARINI INDUSTRIE FARMACEUTICHE RIUNITE S.R.L.

  公开号：WO1997005160A1

  公开（公告）日：1997-02-13

  (EN) Bicyclic lactams containing an arginine residue, which can be of use in therapy as thrombin inhibitors, are disclosed.(FR) L'invention porte sur des lactames bicycliques contenant un reste arginine qui peuvent être utilisés, dans un traitement, comme inhibiteurs de thrombine.
• Chirospecific Syntheses of Conformationally Constrained 7-Azabicycloheptane Amino Acids by Transannular Alkylation
  作者：Jeffrey A. Campbell、Henry Rapoport

  DOI：10.1021/jo960759m

  日期：1996.1.1

  A new method is reported for the chirospecific preparation of optically pure 1-carboxy-7-azabicycloheptane amino acids for the generation of peptidomimetics as conformational probes. The method allows for the multigram preparation of these amino acid analogues through use of a thiolactam sulfide contraction and a transannular alkylation sequence as the key C-C bond-forming steps, starting from L-glutamic

  报道了一种新的方法，用于光学纯的1-羧基-7-氮杂双环庚烷氨基酸的手性制备，以产生拟肽作为构象探针。所述方法允许通过使用硫代内酰胺硫化物收缩和跨环烷基化序列作为关键的CC键形成步骤，从L-谷氨酸开始，对这些氨基酸类似物进行多谱图制备。该路线提供了通往两个常见中间体的途径，即7-（苄氧羰基）-1-羧基-7-氮杂双环[2.2.1] -3-庚烷和（1S，4R）-7-（苄氧羰基）-1-羧基-7-氮杂双环[2.2.1] -3-庚酮叔丁酯，分别用于修饰对称和手性氨基酸同源物。后者中间体的C-1羧基单元的脱羧也证明该方法适用于短时，