1-乙氧基羰基哌啶-2-羧酸 | 130497-14-2

• 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: 1-乙氧基羰基哌啶-2-羧酸
• 中文别名: 1-(乙氧羰基)哌啶-2-羧酸
• 英文名称: (+/-)-[(N-ethoxycarbonyl)piperidine]-2-carboxylic acid
• 英文别名: 1-(ethoxycarbonyl)pipecolic acid；1-(Ethoxycarbonyl)piperidine-2-carboxylic acid；1-ethoxycarbonylpiperidine-2-carboxylic acid
• CAS: 130497-14-2
• 化学式: C₉H₁₅NO₄
• mdl: MFCD09814594
• 分子量: 201.222
• InChiKey: QIINMEGWTDLIJO-UHFFFAOYSA-N

物化性质

• 沸点：
  343.0±35.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  1-乙氧基羰基哌啶-2-羧酸 在 lithium aluminium tetrahydride 、 碘代三甲硅烷 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 71.0h， 生成 (+/-)-[2-(N',N'-dipropylaminomethyl)piperidin-1-yl]-acetonitrile
  参考文献：
  名称：

  Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M 2 receptors

  摘要：

  Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carabonyl]-6H-pyrido[2,3- b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the alpha-highly sulphated cyclodextrin (alpha-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00307-7
• 作为产物：
  描述：

  氯甲酸乙酯 、 六氢吡啶-alpha-羧酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 1-乙氧基羰基哌啶-2-羧酸
  参考文献：
  名称：

  （2S）-1-（芳基乙酰基）-2-（氨基甲基）哌啶衍生物：新颖的高选择性κ阿片类镇痛药。

  摘要：

  本文描述了新型的1-（芳基乙酰基）-2-（氨基甲基）哌啶衍生物的合成和构效关系，作为κ阿片类镇痛药。通过计算研究和1H NMR定义了具有60度扭转角（N1C2C7N8）的药效团的活性构象。芳香族部分取代的定量结构-活性关系研究表明，对位和/或间位存在吸电子和亲脂性取代基是良好的镇痛活性和κ亲和力所必需的。铅化合物（2S）-1-[（（3,4-二氯苯基）乙酰基] -2-（吡咯烷-1-基甲基）哌啶盐酸盐和（2S）-1- [4-（三氟甲基）苯基]乙酰基] -2 -（吡咯烷-1-基甲基）哌啶盐酸盐的Kappa / mu选择性最高（分别为6500：1和4100：1）以及迄今为止鉴定出的最有力的（κκ0.24和0.57 nM）κ配体。在抗伤害感受的小鼠甩尾模型中，化合物14（ED50 = 0.05 mg / kg sc）的效力是吗啡的25倍，效力是标准Kappa配体U-50488的16倍。

  DOI：

  10.1021/jm00105a061

文献信息

• [EN] 1,4-DIARYL-DIHYDROPYRIMIDIN-2-ONES AND THEIR USE AS HUMAN NEUTROPHIL ELASTASE INHIBITORS<br/>[FR] 1,4-DIARYL-DIHYDROPYRIMIDIN-2-ONES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ELASTASE DU NEUTROPHILE HUMAINE
  申请人：BAYER HEALTHCARE AG

  公开号：WO2005082864A1

  公开（公告）日：2005-09-09

  The invention relates to novel heterocyclic derivatives of the general formula (I), processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction and heart failure development.

  这项发明涉及一般式(I)的新型杂环衍生物，其制备方法以及它们在药物中的应用，特别是用于治疗慢性阻塞性肺病、急性冠状动脉综合征、急性心肌梗死和心力衰竭的发展。
• N-acyl-substituted azacyclic compounds, processes for their preparaion,
  申请人：Dr Lo Zambeletti S.p.A.

  公开号：US05366981A1

  公开（公告）日：1994-11-22

  A compound, a solvate or salt thereof, of formula (I): ##STR1## in which: A is ##STR2## p is 2; ROC-- is an acyl group linked to a substituted or unsubstituted carbocyclic aromatic ring system; R.sub.1 and R.sub.2 are substituents on the same or different carbon atoms and are independently hydrogen or C.sub.1-6 alkyl; and R.sub.a is a phenyl or thienyl ring, and is useful for the treatment of pain, hyponatremic disease states or cerebral ischemia.

  公式（I）的复合物，溶剂合物或其盐：##STR1## 其中：A是##STR2## p为2; ROC--是与取代或未取代的碳环芳香基环连接的酰基基团; R.sub.1和R.sub.2是在同一或不同的碳原子上的取代基，且分别独立地是氢或C.sub.1-6烷基; R.sub.a是苯环或噻吩环，并且用于治疗疼痛，低钠血症疾病状态或脑缺血。
• 1,4-Diaryl-Dihydropyrimidin-2-Ones and Their Use as Human Neutrophil Elastase Inhibitors
  申请人：Gielen-Haertwig Heike

  公开号：US20080064704A1

  公开（公告）日：2008-03-13

  The invention relates to novel heterocyclic derivatives of the general formula (I), processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction and heart failure development.

  本发明涉及一种新颖的杂环衍生物，其一般式为（I），以及它们的制备方法和在药物中的应用，特别是用于治疗慢性阻塞性肺疾病、急性冠状动脉综合征、急性心肌梗死和心力衰竭的发展。
• Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants
  作者：Bin Ho、Prabha M. Venkatarangan、Sharon F. Cruse、Christine N. Hinko、Peter H. Andersen、Albert M. Crider、Ahmad A. Adloo、David S. Roane、James P. Stables

  DOI：10.1016/s0223-5234(99)80072-5

  日期：1998.1

  A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2-piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6-dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 and 34 led to a decrease in the MES activity. In the N-(alpha-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the alpha-position of the N-(alpha-methylbenzyl) group does not significantly affect MES activity. (C) Elsevier, Paris.
• N-ACYL-SUBSTITUTED AZACYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, AND THEIR USE AS PHARMACEUTICALS
  申请人：Smithkline Beecham S.p.A.

  公开号：EP0501997B1

  公开（公告）日：1997-01-29