tert-butyl (S)-2-(4-phenyloxazol-2-yl)pyrrolidine-1-carboxylate | 1042690-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (S)-2-(4-phenyloxazol-2-yl)pyrrolidine-1-carboxylate
• 英文别名: (S)-2-(4-Phenyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester；tert-butyl (2S)-2-(4-phenyl-1,3-oxazol-2-yl)pyrrolidine-1-carboxylate
• CAS: 1042690-69-6
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: YCUNBXQFPGUXGI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(4-phenyloxazol-2-yl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-phenyl-2-(pyrrolidin-2-yl)oxazole
  参考文献：
  名称：

  The design of potent and selective inhibitors of DPP-4: Optimization of ADME properties by amide replacements

  摘要：

  For a series of beta-homophenylalanine based inhibitors of dipeptidyl peptidase IV ADME properties were improved by the incorporation of amide replacements. These efforts led to a novel series of potent and selective inhibitors of DPP-4 that exhibit an attractive pharmacokinetic profile and show excellent efficacy in an animal model of diabetes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.078
• 作为产物：
  描述：

  (S)-2-((R)-4-Phenyl-4,5-dihydro-oxazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 过氧化镍 silica gel 、 cyclohexane, ethyl acetate 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 tert-butyl (S)-2-(4-phenyloxazol-2-yl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Dpp-IV Inhibitors

  摘要：

  本发明涉及公式(I)的化合物，其中Z、R1-9、n、A、X和Rb的含义如所述描述和权利要求中所述。所述化合物可用作DPP-IV抑制剂。本发明还涉及制备这些化合物的方法，以及作为药物的生产和使用。

  公开号：

  US20080015146A1

文献信息

• A novel synthetic method of 2,4-disubstituted oxazoles using carboxylic acid-derived Bu2Sn[OC(O)R]2
  作者：Hiroki Yoneyama、Naoki Oka、Yoshihide Usami、Shinya Harusawa

  DOI：10.1016/j.tetlet.2020.151983

  日期：2020.6

  A novel synthetic method for the preparation of 2,4-disubstituted oxazoles was developed, entailing the reaction of dibutyltin diacylates Bu2Sn[OC(O)R](2) with 1-substituted acetylenes and TMSN3 to afford a range of 2,4-disubstituted oxazoles in good yields. (C) 2020 Elsevier Ltd. All rights reserved.
• WO2008/93960
  申请人：——

  公开号：——

  公开（公告）日：——
• DPP-IV INHIBITORS
  申请人：Santhera Pharmaceuticals (Schweiz) AG

  公开号：EP1786806A1

  公开（公告）日：2007-05-23
• [EN] DPP-IV INHIBITORS<br/>[FR] INHIBITEURS DE LA DPP-IV
  申请人：SANTHERA PHARMACEUTICALS DEUTS

  公开号：WO2005121131A1

  公开（公告）日：2005-12-22

  The invention relates to compounds of formula (I); wherein Z, R1-9, n, A, X and Rb have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.
• The design of potent and selective inhibitors of DPP-4: Optimization of ADME properties by amide replacements
  作者：Sonja Nordhoff、Stephan Bulat、Silvia Cerezo-Gálvez、Oliver Hill、Barbara Hoffmann-Enger、Meritxell López-Canet、Claudia Rosenbaum、Christian Rummey、Meinolf Thiemann、Victor G. Matassa、Paul J. Edwards、Achim Feurer

  DOI：10.1016/j.bmcl.2009.09.078

  日期：2009.11

  For a series of beta-homophenylalanine based inhibitors of dipeptidyl peptidase IV ADME properties were improved by the incorporation of amide replacements. These efforts led to a novel series of potent and selective inhibitors of DPP-4 that exhibit an attractive pharmacokinetic profile and show excellent efficacy in an animal model of diabetes. (C) 2009 Elsevier Ltd. All rights reserved.