2-哌啶羧酸,1-甲基-,甲基酯,(2S)- | 157026-38-5

• 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: 2-哌啶羧酸,1-甲基-,甲基酯,(2S)-
• 英文名称: (S)-Methyl N-methylpipecolate
• 英文别名: methyl (2S)-1-methylpiperidine-2-carboxylate
• CAS: 157026-38-5
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: YZEGGKQFWJCIQG-ZETCQYMHSA-N

物化性质

• 沸点：
  190.0±33.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-哌啶羧酸,1-甲基-,甲基酯,(2S)- 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (2S)-N-甲基-2-哌啶甲醇
  参考文献：
  名称：

  Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry

  摘要：

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

  DOI：

  10.1021/jo00123a008
• 作为产物：
  描述：

  氯甲酸甲酯 、 (R)-N-Methyl-2-(tributylstannyl)piperidine 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 2-哌啶羧酸,1-甲基-,甲基酯,(2S)-
  参考文献：
  名称：

  Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry

  摘要：

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

  DOI：

  10.1021/jo00123a008

文献信息

• COMPOUNDS AND METHODS FOR ANTIVIRAL TREATMENT
  申请人：GILEAD SCIENCES, INC.

  公开号：US20130273037A1

  公开（公告）日：2013-10-17

  Compounds and pharmaceutically acceptable salts and esters and compositions thereof, for treating viral infections are provided. The compounds and compositions 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.

  提供用于治疗病毒感染的化合物、药用可接受的盐和酯及其组合物。这些化合物和组合物对于治疗Pneumovirinae病毒感染很有用。提供的化合物、组合物和方法特别适用于治疗人类呼吸道合胞病毒感染。
• [EN] METALLOENZYME INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE MÉTALLOENZYME
  申请人：VIAMET PHARMACEUTICALS INC

  公开号：WO2014117090A1

  公开（公告）日：2014-07-31

  The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

  这项即时发明描述了具有金属酶调节活性的化合物，以及治疗由这些金属酶介导的疾病、疾病或症状的方法。
• [EN] LINEAR APELIN RECEPTOR AGONISTS<br/>[FR] AGONISTES LINÉAIRES DU RÉCEPTEUR DE L'APELINE
  申请人：HEPTARES THERAPEUTICS LTD

  公开号：WO2022079428A1

  公开（公告）日：2022-04-21

  The disclosures herein relate to novel compounds of formula (1): and salts thereof, wherein Q, X, AA1, AA2, AA3, AA4, AA5, AA6, AA7, AA8, AA9, AA10, AA11, AA12, AA13, R1R2and n are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with Apelin receptors.

  本公开涉及式（1）的新化合物及其盐，其中Q、X、AA1、AA2、AA3、AA4、AA5、AA6、AA7、AA8、AA9、AA10、AA11、AA12、AA13、R1R2和n在此处定义，并其在治疗、预防、改善、控制或减少与Apelin受体相关的疾病风险方面的用途。
• THROMBIN INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150038498A1

  公开（公告）日：2015-02-05

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: (I) or a pharmaceutically acceptable salt thereof, wherein Q is CH 2 , NR 4 , O, S, S(O) or S(O 2 ), wherein R 4 is H, C 1-6 alkyl, aryl, or C 3-8 cycloalkyl; R 1 is a heterocycle or —(CR 5 R 6 )1-2NH2, wherein R 5 and R 6 , each time in which they occur, are independently H, C 1-6 alkyl, —CH 2 F, —CHF 2 , CF 3 or —CH 2 OH; R 2 is OH, NH 2 or NHSO 2 CH 3 ; and R 3 is C 1-6 alkyl.

  本发明的化合物具有以下结构（I）或其药学上可接受的盐，在抑制凝血酶和相关的血栓闭塞方面有用，其中Q为CH2，NR4，O，S，S（O）或S（O2），其中R4为H，C1-6烷基，芳基或C3-8环烷基；R1为杂环或-（CR5R6）1-2NH2，其中R5和R6在每次出现时独立地为H，C1-6烷基，-CH2F，-CHF2，CF3或-CH2OH；R2为OH，NH2或NHSO2CH3；R3为C1-6烷基。
• [EN] COMPOUND USED AS SIRT6 SMALL-MOLECULE ALLOSTERIC ACTIVATOR AND PHARMACEUTICAL COMPOSITION THEREOF<br/>[FR] COMPOSÉ UTILISÉ EN TANT QU'ACTIVATEUR ALLOSTÉRIQUE À PETITE MOLÉCULE DE SIRT6 ET COMPOSITION PHARMACEUTIQUE CORRESPONDANTE<br/>[ZH] 用作SIRT6小分子别构激动剂的化合物及其药物组合物
  申请人：SHANGHAI JIAOTONG UNIV SCHOOL OF MEDICINE

  公开号：WO2019029211A1

  公开（公告）日：2019-02-14

  本发明公开了SIRT6小分子别构激动剂及其应用，提供一种含有式(1)所示的衍生物或其药理学上可接受的盐为有效成分的SIRT6小分子别构激动剂。本发明设计并合成高效低毒的SIRT6小分子别构激动剂，在体外实验中能够明显激动SIRT6的活性，对相关疾病药物的开发具有重要的意义。