(2R,5R)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester | 851544-25-7

• 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: (2R,5R)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,5S)-1-(2-methoxy-2-oxoacetyl)-5-prop-2-enylpyrrolidine-2-carboxylate
• CAS: 851544-25-7
• 化学式: C₁₅H₂₃NO₅
• 分子量: 297.351
• InChiKey: IPQANGFCMNLXGQ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester 在 锂硼氢 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,5S)-5-Allyl-1-(2-oxo-acetyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683
• 作为产物：
  描述：

  L-N-(tert-butyloxycarbonyl)-5-allyl-proline tert-butyl ester 、 甲基戊酰氯 在 高氯酸 、 Amberlyst A-21 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到(2R,5R)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683

文献信息

• [EN] PEPTIDOMIMETIC COMPOUNDS, STEREOSELECTIVE PROCESS FOR THEIR PREPARATION, THEIR USE AS BIOLOGICALLY ACTIVE SYNTHETIC INTERMEDIATES<br/>[FR] COMPOSES PEPTIDOMIMETIQUES, LEUR PROCEDE STEREOSELECTIF DE PREPARATION, ET LEURS APPLICATIONS COMME INTERMEDIAIRES DE SYNTHESE A ACTIVITE BIOLOGIQUE
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2005042531A1

  公开（公告）日：2005-05-12

  The invention relates to novel cyclic peptidomimetic compounds having an azabicycloalkane structure, useful as intermediates in the preparation of αVΒ3 and αVΒ5 integrin antagonists, intended, for example, for the treatment of altered angiogenic phenomena; the invention also concerns a process for the stereoselective synthesis of said cyclic peptidomimetic compounds and biologically active derivatives thereof. Formula (I) wherein: n is 1 or 2, R1 is H, (C1-C4)alkyl,benzyl or a protective group; R2 is H or a protective group; R3 is H or heteroalkyl or a protective group; Their salts, racemic mixtures,individual enantiomers ,individual diastereoisomers and mixtures thereof in any proportion.

  该发明涉及具有氮杂环辛烷结构的新型环肽类似物化合物，可作为制备αVΒ3和αVΒ5整合素拮抗剂的中间体，例如用于治疗改变的血管生成现象；该发明还涉及一种用于立体选择性合成所述环肽类似物化合物及其生物活性衍生物的方法。公式（I）中：n为1或2，R1为H，（C1-C4）烷基，苄基或保护基；R2为H或保护基；R3为H或杂原子烷基或保护基；它们的盐，消旋混合物，单对映体，单顺异构体及其以任何比例混合。
• INTRA-OPERATIVE IMAGING
  申请人：BRACCO IMAGING S.P.A.

  公开号：US20170340755A1

  公开（公告）日：2017-11-30

  The present invention relates to the use of a NIR fluorescent probe comprising an aza-bicycloalkane based cyclic peptide labelled with a Cy5.5 dye moiety in the fluorescence- guided surgery of pathologic regions and to an optical imaging method that comprises using this fluorescent probe for the identification and demarcation of tumor margins during the surgical resection.