(R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester | 639458-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester；(R)-N-tert-butoxycarbonyl-2-[(R)-piperidin-2-yl]acetaldehyde；(R)-tert-butyl-2-(formylmethyl)piperidine-1-carboxylate；tert-butyl (2R)-2-(2-oxoethyl)piperidine-1-carboxylate
• CAS: 639458-46-1
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: VPUHJQDNBOTMSI-SNVBAGLBSA-N

物化性质

• 沸点：
  318.1±15.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 1-piperidin-2-yl-propan-2-ol
  参考文献：
  名称：

  Short enantioselective synthesis of sedridines, ethylnorlobelols and coniine via reagent-based differentiation

  摘要：

  The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tertbutyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.032
• 作为产物：
  描述：

  (R)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 在 sodium acetate 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 Trametes pubescens laccase 、 氧气 、 sodium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine

  摘要：

  The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alcohol to a ketone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.056

文献信息

• Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate
  作者：Gandham Satyalakshmi、Kanaparthy Suneel、Digambar Balaji Shinde、Biswanath Das

  DOI：10.1016/j.tetasy.2011.06.011

  日期：2011.5

  The stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine and (+)-sedamine has been achieved through a common intermediate generated from butane-1,4-diol. The synthetic sequence involves a Maruoka asymmetric allylation and ring-closing metathesis as the key steps.

  哌啶生物碱，（+）-丝氨酸，（+）-伪conhydrine和（+）-sedamine的立体选择性全合成已通过由1,4-丁烷生成的常见中间体实现。合成序列涉及Maruoka不对称烯丙基化和开环易位作为关键步骤。
• Aminoindane Compounds and Use Thereof in Treating Pain
  申请人：Thompson Scott Kevin

  公开号：US20120214809A1

  公开（公告）日：2012-08-23

  The present application provides novel aminoindane compounds and methods for preparing and using these compounds. These compounds are useful in treating pain and/or itch in patients by administering one or more of the compounds to a patient. The methods include administering a compound of formula (I) or (II) and a TRPV 1 receptor activator. In one embodiment, the TRPV 1 receptor activator is lidocaine.

  本申请提供了新颖的氨基茚化合物以及制备和使用这些化合物的方法。这些化合物可用于通过向患者施用一种或多种化合物来治疗患者的疼痛和/或瘙痒。这些方法包括施用式(I)或(II)的化合物和TRPV 1受体激活剂。在一个实施例中，TRPV 1受体激活剂是利多卡因。
• [EN] USE OF AMINOINDANE COMPOUNDS IN TREATING OVERACTIVE BLADDER AND INTERSTITIAL CYSTITIS<br/>[FR] UTILISATION DE COMPOSÉS D'AMINOINDANE DANS LE TRAITEMENT D'UNE VESSIE HYPERACTIVE ET D'UNE CYSTOPATHIE INTERSTITIELLE SOUS-MUQUEUSE
  申请人：ENDO PHARMACEUTICALS INC

  公开号：WO2014028675A1

  公开（公告）日：2014-02-20

  The present application provides methods of using the aminoindane compounds of formula (I) or (II) in treating an overactive bladder or interstitial cystitis by administering one or more of the compounds to a patient.

  本申请提供了使用式(I)或(II)的氨基茚化合物治疗患有过度活跃膀胱或间质性膀胱炎的方法，通过向患者施用其中一种或多种化合物。
• Asymmetric synthesis of (+)-vertine and (+)-lythrine
  作者：Laëtitia Chausset-Boissarie、Roman Àrvai、Graham R. Cumming、Laure Guénée、E. Peter Kündig

  DOI：10.1039/c2ob25880c

  日期：——

  The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8 : 1 ratio. The major product is used in the synthesis of (+)-vertine via aryl–aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl–aryl coupling failed.

  描述了(+)-vertine和(+)-lythrine这两种Lythracea生物碱的全合成过程。使用对映富集的pelletierine作为手性构建块，并通过两步pelletierine缩合反应，以8:1的比例生成两种喹啉环己二酮二异构体。主要产物通过芳基-芳基偶联和环闭合复分解反应合成(+)-vertine，提供了与内酯羰基功能团α位的Z-烯烃。对主要喹啉环己二酮二异构体进行碱诱导的异构化后，采用相同步骤合成了(+)-lythrine。传统的环闭合策略，如大环内酯化或芳基-芳基偶联都未能成功。
• Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects
  作者：Paweł Zajdel、Tomasz Kos、Krzysztof Marciniec、Grzegorz Satała、Vittorio Canale、Krzysztof Kamiński、Małgorzata Hołuj、Tomasz Lenda、Robert Koralewski、Marek Bednarski、Leszek Nowiński、Jacek Wójcikowski、Władysława A. Daniel、Agnieszka Nikiforuk、Irena Nalepa、Piotr Chmielarz、Justyna Kuśmierczyk、Andrzej J. Bojarski、Piotr Popik

  DOI：10.1016/j.ejmech.2018.01.002

  日期：2018.2

  therapeutic effects, there is no consensus regarding an “ideal” target engagement. Here, a detailed SAR analysis in a series of 45 novel azinesulfonamides of cyclic amine derivatives, involving the aryl-piperazine/piperidine pharmacophore, central alicyclic amine and azinesulfonamide groups has led to the selection of (S)-4-((2-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)pyrrolidin-1-yl)sulfonyl)isoquinoline

  当前使用的抗精神病药的特征在于多受体作用方式。尽管多巴胺D 2受体的拮抗作用可减轻精神分裂症的“阳性”症状，而对其他（尤其是血清素能受体）的作用对于它们的附加治疗作用是必需的，但对于“理想的”靶标结合尚无共识。在此，对涉及环芳基-哌嗪/哌啶药效团，中心脂环族胺和嗪磺酰胺基团的45种新颖的环胺衍生物的新型嗪磺酰胺进行了详细的SAR分析，导致选择了（S）-4-（（2-（ 2-（4-（苯并[ b ]噻吩-4-基）哌嗪-1-基）乙基）吡咯烷-1-基磺酰基）异喹啉（62）。62的多药理学特征是部分5-HT 1A R拮抗作用，5-HT 2A / 5-HT 7 / D 2 / D 3 R拮抗作用和对SERT的阻断，降低了“阳性”样和“阴性”似精神病的症状。化合物62不产生僵直症，显示出高催乳激素缺乏症，并在新颖的物体识别任务和注意力转移试验中表现出促认知作用。虽然仍未完全确定体外特征与有希望的体内分布相