甲基2-哌啶基乙酸酯 | 171730-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 甲基2-哌啶基乙酸酯
• 中文别名: (5S,9R,10S,12R,13S,14S)-17-[(2R)-1,3-二羰基丁烷-2-基]-10,13-二甲基-4,4,8-三[(~2~H_1_)甲基]-2,3,4,5,6,7,8,9,10,11,12,13,14,15-十四氢-1H-环戊二烯并[a]菲-12-基3-羟基丁酸酯(non-preferredname)
• 英文名称: methyl (R)-(2-piperidino)acetate
• 英文别名: methyl [(R)-piperidin-2-yl]acetate；(R)-homopipecolic acid methyl ester；(R)-homopipecolinic acid methyl ester；methyl 2-[(2R)-piperidin-2-yl]acetate
• CAS: 171730-95-3
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: KNLRJTRKAHPHEE-SSDOTTSWSA-N

物化性质

• 沸点：
  213.1±13.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 甲基2-哌啶基乙酸酯 在 甲基2-哌啶基乙酸酯 作用下， 生成 (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(methoxycarbonylmethyl)piperidine
  参考文献：
  名称：

  Pyrazolopyridine compounds which have useful pharmaceutical utility

  摘要：

  本发明涉及一种吡唑吡啶化合物，用于治疗忧郁症、心力衰竭、高血压、肾功能不全、肾毒性、肾病综合征、肾炎、水肿、肥胖症、支气管哮喘、痛风、高尿酸血症、婴儿猝死综合症、免疫抑制、糖尿病、心肌梗死、血栓形成、梗阻、动脉硬化闭塞、血栓性静脉炎、脑梗死、短暂性脑缺血发作或心绞痛。该化合物的分子式为##STR1## 其中基团的定义见权利要求。

  公开号：

  US05234930A1
• 作为产物：
  描述：

  5-氯戊酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 氢气 、 四丁基碘化铵 、 对甲苯磺酸 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 甲基2-哌啶基乙酸酯
  参考文献：
  名称：

  Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines

  摘要：

  A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of omega-chloro-beta-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethylamine or (S)-1-(1-naphthyl)ethylamine and omega-chloro-beta-keto esters 5 and 10, respectively and (ii) a highly diastereoselective NaBH4 reduction followed by hydrogenolysis. The present method is a short-step process using inexpensive and readily available substrates and reagents with fewer wasted materials. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.014
• 作为试剂：
  描述：

  、 甲基2-哌啶基乙酸酯 在 甲基2-哌啶基乙酸酯 作用下， 生成 (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(methoxycarbonylmethyl)piperidine
  参考文献：
  名称：

  Pyrazolopyridine compound and processes for preparation thereof

  摘要：

  该披露涉及公式为##STR1##的吡唑吡啶化合物，其中变量在说明书中定义。该化合物可用于治疗支气管哮喘、免疫抑制、糖尿病等疾病。

  公开号：

  US04994453A1

文献信息

• [EN] IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL<br/>[FR] AMÉLIORATIONS APPORTÉES OU SE RAPPORTANT AUX MATÉRIAUX ORGANIQUES
  申请人：UNIV LIEGE

  公开号：WO2018050546A1

  公开（公告）日：2018-03-22

  The invention provides a method for the preparation of an intermediate for use in synthesizing a lower alkyl phenidate compound of formula (I), wherein each R1 independently represents an optionally substituted aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, sulfo or sulfhydryl group, R2 represents a hydrogen atom or a lower alkyl group, n represents an integer from 1 to 5 and m represents an integer from 1 to 3 or a pharmaceutically acceptable salt thereof; which method comprises the steps of: (a) flowing a tosylhydrazone compound of formula (IV), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I), an organic base and an organic solvent into a fluidic network; and (b) reacting the tosylhydrazone compound of formula (IV) and the base in the fluidic network under thermal and/or photochemical conditions to form a transient diazoamide compound of formula (V), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I).

  该发明提供了一种制备用于合成化合物的中间体的方法，该化合物是具有如下式(I)的较低烷基苯二酸酯化合物，其中每个R1都独立地代表一个可选择取代的芳基、杂环芳基、烷基、环烷基、烷氧基、芳氧基、酰基、羧基、羟基、卤素、氨基、硝基、磺酰基或硫氢基，R2代表氢原子或较低烷基基团，n表示1到5的整数，m表示1到3的整数或其药用可接受的盐；所述方法包括以下步骤：(a)将如下式(IV)中定义的R1、n和m与上述关于如下式(I)的甲基苯二酸酯相关的甲磺酰腙化合物、有机碱和有机溶剂导入到流体网络中；以及(b)在热和/或光化学条件下在流体网络中将如下式(IV)中定义的甲磺酰腙化合物和碱反应以形成如下式(V)的瞬时重氮酰胺化合物，其中R1、n和m如上述关于如下式(I)的甲基苯二酸酯相关的定义。
• Convenient Multigram Synthesis of (<i>R</i>)-Homopipecolic Acid Methyl Ester
  作者：Matthias Breuning、Melanie Steiner

  DOI：10.1055/s-2006-926419

  日期：2006.4

  (R)-Homopipecolic acid methyl ester has been prepared on a multigram scale from 3,4-dihydro-2H-pyran in five steps and 36% overall yield. The stereochemistry was introduced via an asymmetric Michael addition and a fractional crystallization.

  (R)-高哌啶酸甲酯已由 3,4-二氢-2H-吡喃以 5 步和 36% 的总产率以多克规模制备。通过不对称迈克尔加成和分级结晶引入立体化学。
• Potential of (2E,7E)-Nonadienedioates in Asymmetric Synthesis: Construction of Homopipecolic Acid and an Aminoester Building Block for Peptide Nucleic Acids
  作者：Narciso Garrido、Alfonso Rubia、Carlos Nieto、David Díez

  DOI：10.1055/s-0029-1219375

  日期：2010.3

  A convenient, asymmetric synthesis of (R)-homopipecolic acid methyl ester and an homochiral peptide nucleic acid (PNA) monomer building block are described, starting from the orthogonally disubstituted (2E,7E)-nonadienedioate. The approach involves stereoselective Michael monoaddition of (R)-N-benzyl-N-α-methylbenzylamide to the unsaturated ester as the key step, and subsequent transformation of the remaining double bond of the unsaturated acid.

  本文介绍了从正交二取代(2E,7E)-壬二烯酸酯开始，方便地不对称合成(R)-高哌羧酸甲酯和同手性肽核酸 (PNA) 单体结构单元的方法。该方法的关键步骤是将(R)-N-苄基-N-δ-±-甲基苄酰胺与不饱和酯进行立体选择性迈克尔单加成，然后再将不饱和酸的剩余双键进行转化。
• Chemoenzymatic approach to enantiopure piperidine-based β-amino esters in organic solvents
  作者：Arto Liljeblad、Hanna-Maija Kavenius、Petri Tähtinen、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2007.01.027

  日期：2007.2

  This research concentrates on the enantioselectivities of lipase-catalysed reactions with methyl esters of 2-piperidylacetic acid and 3-piperidinecarboxylic acid derivatives. N-Acetylated 2-piperidylacetic acid methyl ester displayed good enantioselectivity (E = 66) in a 1:1 mixture of diisopropyl ether and butyl butanoate in the presence of lipase PS-C IT from Burkholderia cepacia. The reaction is known as interesterification with butyl butanoate rather than alcoholysis with the butanol, because butyl butanoate has to be first hydrolysed or go through alcoholysis with MeOH in order to release butanol. Other N-protective groups (Boc, Ns, Fmoc and Bzn) gave excellent en anti oselectivity (E > 200) under the same conditions, and a gram-scale resolution was performed with N-Boc-2-piperidylacetic acid methyl ester. Reaction with a 3-piperidylcarboxylic acid derivative took place with disappointingly low enantioselectivity (E = 4), with Candida antarctica lipase B being the best of the lipases screened. (c) 2007 Elsevier Ltd. All rights reserved.