4-甲基-2-哌啶羧酸 | 172823-76-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 4-甲基-2-哌啶羧酸
• 英文名称: (2R,4R)-4-Methyl-piperidine-2-carboxylic acid
• 英文别名: 4-Methyl-2-piperidine carboxylic acid；4-methylpiperidine-2-carboxylic acid；4-methylpiperidin-1-ium-2-carboxylate
• CAS: 172823-76-6
• 化学式: C₇H₁₃NO₂
• mdl: MFCD04118088
• 分子量: 143.186
• InChiKey: UQHCHLWYGMSPJC-UHFFFAOYSA-N

物化性质

• 沸点：
  267.0±33.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-2-哌啶羧酸 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2S)-2-[[4-methyl-1-(3-methylbutyl)piperidine-2-carbonyl]amino]-3-(4-phenylmethoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers

  摘要：

  Selective N-type Voltage Activated Calcium Channel (VACC) blockers have shown utility in several models of stroke and pain. In the process of searching for small molecules as N-type calcium channel blockers, we have identified a series of N,N-dialkylpeptidylamines (e.g., PD 175069) with potent functional activity at N-type VACC. Further modification of the leucine moiety of PD 175069 with a cyclized ring structure provides a series of novel molecules. Syntheses and pharmacological evaluation of the series are presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00160-2
• 作为产物：
  描述：

  4-甲基甲酸吡啶盐酸盐 以92%的产率得到
  参考文献：
  名称：

  SHUMAN, ROBERT T.;ORNSTEIN, PAUL L.;PASCHAL, JONATHAN W.;GESELLCHEN, PAUL+, J. ORG. CHEM., 55,(1990) N, C. 738-741

  摘要：

  DOI：

文献信息

• [EN] PYRAZOLO [1, 5 -A] PYRIMIDINES AS ANTIVIRAL AGENTS<br/>[FR] PYRAZOLO[1,5-A]PYRIMIDINES EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GILEAD SCIENCES INC

  公开号：WO2011163518A1

  公开（公告）日：2011-12-29

  The invention provides compounds of Formula I or Formula II: (I), (II) or a pharmaceutically acceptable salt or ester, thereof, as described herein. The compounds and compositions thereof are useful for treating Pneumovirinae virus infections. The compounds, compositions, and methods provided are particularly useful for the treatment of Human respiratory syncytial virus infections.

  本发明提供了公式I或公式II的化合物：(I)、(II)或其药用可接受的盐或酯，如本文所述。这些化合物及其组合物可用于治疗副粘病毒感染。这些化合物、组合物和方法特别适用于治疗人类呼吸道合胞病毒感染。
• PROCESS INTERMEDIATES AND METHODS FOR THE PREPARATION OF PROCESS INTERMEDIATES FOR THE SYNTHESIS OF ARGATROBAN MONOHYDRATE
  申请人：Stivanello Mariano

  公开号：US20140088310A1

  公开（公告）日：2014-03-27

  Methods are provided for the synthesis of key intermediates for the synthesis of Argatroban monohydrate, ethyl (2R,4R)-1-[(2S)-2-amino-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methylpiperidine-2-carboxylate compounded with HCl. Such intermediates are also provided.

  提供了一种合成Argatroban monohydrate的关键中间体的方法，该中间体是乙酸(2R,4R)-1-[(2S)-2-氨基-5-[[亚硝基氨基)甲基]氨基]-1-氧代戊基]-4-甲基哌啶-2-羧酸乙酯，与HCl混合。同时也提供了这些中间体。
• [EN] METHOD FOR THE PREPARATION OF PROCESS INTERMEDIATES FOR THE SYNTHESIS OF ARGATROBAN MONOHYDRATE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES DE PROCÉDÉ POUR LA SYNTHÈSE DE L'ARGATROBAN MONOHYDRATE
  申请人：LUNDBECK PHARMACEUTICALS ITALY S P A

  公开号：WO2012136504A1

  公开（公告）日：2012-10-11

  Object of the present invention is a method for the synthesis of a key intermediate for the synthesis of Argatroban monohydrate, ethyl (2R,4R)-1-[(2S)-2-amino-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4- methylpiperidine-2-carboxylate compounded with HCl.

  本发明的对象是一种用于合成Argatroban monohydrate的关键中间体的方法，该中间体为乙酸(2R,4R)-1-[(2S)-2-氨基-5-[[亚硝胺基]亚氨基]-1-氧代戊基]-4-甲基哌啶-2-羧酸乙酯，并与HCl复合。
• A process for the preparation of trans-(2R)-4-substituted-pipecolic acids and esters thereof, and intermediate compounds used therein
  申请人：Enantia, S.L.

  公开号：EP2305646A1

  公开（公告）日：2011-04-06

  Process for the preparation of a compound of formula (III) wherein R1 is a (C1-C10)-alkyl radical or a radical of one of the known ring systems with 1-3 rings, the rings being aromatic and being isolated or partially/totally fused and having 5-6 members, being each member independently selected from C, CH, N, NH, O, S; and the ring system being optionally substituted by one or more radicals independently selected from (C1-C6)-alkyl, (C1-C6)-alkoxy, and halogen; the process comprising: a) reacting a (C1-C10)-alkyl lithium, or a lithium salt of the ring system as defined above with a copper salt to obtain an organocuprate compound, and b) reacting the organocuprate compound obtained in step a) with di(tert-butyl) (2R)-3,6-dihydro-6-oxo-1,2(2H)-pyridinedicarboxylate_in an inert solvent system in the presence of a Lewis acid. Intermediate IV is new and is useful as an intermediate for the preparation of pharmaceutically active ingredients such as Argatroban.

  制备III式化合物的过程，其中R1是(C1-C10)-烷基基团或已知环系统之一的基团，环系统具有1-3个环，环是芳香的，可以是孤立的或部分/完全融合的，每个环成员独立地选择自C、CH、N、NH、O、S；并且该环系统可以选择性地被一个或多个基团取代，这些基团独立地选择自(C1-C6)-烷基、(C1-C6)-烷氧基和卤素；该过程包括：a）将(C1-C10)-烷基锂或上述环系统的锂盐与铜盐反应以获得有机铜化合物，b）在惰性溶剂体系中，在Lewis酸存在下，将步骤a）中获得的有机铜化合物与二(叔丁基)(2R)-3,6-二氢-6-氧代-1,2(2H)-吡啶二羧酸酯反应。中间体IV是新的，并且可用作制备药用活性成分如阿加曲铁的中间体。
• [EN] A PROCESS FOR THE PREPARATION OF TRANS-(2R)-4-SUBSTITUTED-PIPECOLIC ACIDS AND ESTERS THEREOF, AND INTERMEDIATE COMPOUNDS USED THEREIN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDES (2R)-PIPÉCOLIQUES TRANS, SUBSTITUÉS EN POSITION 4, ET DE LEURS ESTERS, ET COMPOSÉS INTERMÉDIAIRES UTILISÉS À CET EFFET
  申请人：ENANTIA S L

  公开号：WO2011039290A1

  公开（公告）日：2011-04-07

  Process for the preparation of a compound of formula (III) wherein R1 is a (C1- C10)-alkyl radical or a radical of one of the known ring systems with 1 -3 rings, the rings being aromatic and being isolated or partially/totally fused and having 5-6 members, being each member independently selected from C, CH, N, NH, O, S; and the ring system being optionally substituted by one or more radicals independently selected from (C1-C6)-alkyl, (C1-C6)-alkoxy, and halogen; the process comprising: a) reacting a (C1-C10)-alkyl lithium, or a lithium salt of the ring system as defined above with a copper salt to obtain an organocuprate compound, and b) reacting the organocuprate compound obtained in step a) with di(tert-butyl) (2R)-3,6-dihydro-6-oxo-1,2(2H)- pyridinedicarboxylatejn an inert solvent system in the presence of a Lewis acid. Intermediate IV is new and is useful as an intermediate for the preparation of pharmaceutically active ingredients such as Argatroban.

  制备式（III）化合物的过程，其中R1是（C1-C10）烷基或已知环系之一的基团，该环系具有1-3个环，环为芳香环且为隔离或部分/完全融合，其中每个环成员独立地选择自C，CH，N，NH，O，S，环系可由一个或多个基团独立地选择自（C1-C6）烷基，（C1-C6）烷氧基和卤素进行取代；该过程包括：a）反应（C1-C10）烷基锂或上述定义的环系的锂盐与铜盐反应以获得有机铜化合物，b）在惰性溶剂体系中，在路易斯酸的存在下，将步骤a）中获得的有机铜化合物与二（叔丁基）（2R）-3,6-二氢-6-氧代-1,2（2H）-吡啶二甲酸酯反应。中间体IV是新的，可用作制备药物活性成分，如阿加曲班的中间体。