(S)-1-tert-butyl 2-[(2-phenylethyl)carbamoyl]pyrrolidine-1-carboxylate | 92122-49-1

• 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: (S)-1-tert-butyl 2-[(2-phenylethyl)carbamoyl]pyrrolidine-1-carboxylate
• 英文别名: 1-(tert-butyloxycarbonyl)-N-(2-phenylethyl)-L-prolinamide；tert-butyl (2S)-2-(2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 92122-49-1
• 化学式: C₁₈H₂₆N₂O₃
• 分子量: 318.416
• InChiKey: XPJJIRYVQMQRBO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butyl 2-[(2-phenylethyl)carbamoyl]pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S)-N-(2-phenylethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  ( S )-1-甲酰基吡咯烷-2-羧酸衍生物的合成和催化活性对酮和酮亚胺的对映选择性还原

  摘要：

  一系列 (S)-1-甲酰基吡咯烷-2-羧酸衍生物 (6a-t) 已被合成并作为手性有机催化剂用于酮 2 和酮亚胺 3 的不对称还原。这些有机活化剂提供了良好到中等的对映选择性酮和酮亚胺的不对称还原。其中，有机活化剂6h显示出最佳的效率，在酮的还原中提供了84％的收率和41％的ee，在酮亚胺的还原中提供了75％的收率和52％的ee。

  DOI：

  10.3184/030823408x318433
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 吡啶 作用下， 反应 5.75h， 生成 (S)-1-tert-butyl 2-[(2-phenylethyl)carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  磷酸酯-羧酸酯混合酸酐法：温和有效的酯和酰胺键构建工艺

  摘要：

  描述了一种高效的羧酸酯-磷酸酐途径，可从羧酸，醇或胺直接，经济地合成酯和酰胺。该反应在保留手性仲醇和α-氨基酸衍生物的构型的情况下进行，从而允许获得有用的手性助剂，配体和有机催化剂。由于副产物的水溶性，可以直接高产率地分离出酯和酰胺产物。

  DOI：

  10.1016/j.tet.2012.04.103

文献信息

• Analgesic dipeptide amides and method of use and compositions thereof
  申请人：Sterling Drug Inc.

  公开号：US04450155A1

  公开（公告）日：1984-05-22

  A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula R.sub.1 TyrProNR.sub.4 R.sub.5 wherein R.sub.1 is hydrogen or alkyl, R.sub.4 is phenylalkyl or substituted-phenylalkyl and R.sub.5 is hydrogen, alkyl, phenylalkyl or substituted-phenylalkyl are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.

  一种二肽酰胺的属，包括首选亚属具有结构式R.sub.1 TyrProNR.sub.4 R.sub.5的二肽酰胺，其中R.sub.1为氢或烷基，R.sub.4为苯基烷基或取代苯基烷基，R.sub.5为氢、烷基、苯基烷基或取代苯基烷基，通过将二肽与胺或氨基酸与氨基酸酰胺缩合制备，并可用作镇痛剂。
• Condensation of α-Amino Acid with Amine in the Absence of a Coupling Agent
  作者：Jun-ichi Yamaguchi、Shinya Nagai、Emi Fukuoka、Takayuki Suyama

  DOI：10.1246/cl.2003.830

  日期：2003.9

  Treatment of N-(4-nitrophenoxycarbonyl)amino acid with an equimolar amount of amine in the absence of a coupling agent gave the corresponding α-amino acid amide in high yield.

  在没有偶联剂的情况下，用等摩尔量的胺处理 N-(4-硝基苯氧羰基)氨基酸，可以高产率地得到相应的 α-氨基酸酰胺。
• 2(S)-(Cycloalk-1-enecarbonyl)-1-(4-phenyl-butanoyl)pyrrolidines and 2(S)-(aroyl)-1-(4-phenylbutanoyl)pyrrolidines as prolyl oligopeptidase inhibitors
  作者：Elina M. Jarho、Jarkko I. Venäläinen、Sami Poutiainen、Harri Leskinen、Jouko Vepsäläinen、Johannes A.M. Christiaans、Markus M. Forsberg、Pekka T. Männistö、Erik A.A. Wallén

  DOI：10.1016/j.bmc.2006.12.036

  日期：2007.3

  In order to replace the P2-P1 amide group, different 1-cycloalkenyls and 2-aryls were studied in the place of the PI pyrrolidine group of a 4-phenylbutanoyl-L-Pro-pyrrolidine structure, which is a well-known prolyl oligopeptidase inhibitor SUAM-1221. The 1-cyclopentenyl and the 2-thienyl groups gave novel compounds, which were equipotent with the corresponding pyrrolidine-analog SUAM-1221. It was shown that the P2-P1 amide group of POP inhibitors can be replaced by an alpha, beta-unsaturated carbonyl group or the aryl conjugated carbonyl group. (c) 2007 Elsevier Ltd. All rights reserved.
• Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity
  作者：Pijus K. Mandal、Pietro Morlacchi、J. Morgan Knight、Todd M. Link、Gilbert R. Lee、Roza Nurieva、Divyendu Singh、Ankur Dhanik、Lydia Kavraki、David B. Corry、John E. Ladbury、John S. McMurray

  DOI：10.1021/acs.jmedchem.5b01321

  日期：2015.11.25

  Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4R alpha bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.
• MORGAN, B. A.
  作者：MORGAN, B. A.

  DOI：——

  日期：——