2-oxopiperidine-1-carboxylic acid ethyl ester | 33485-71-1

• 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: 2-oxopiperidine-1-carboxylic acid ethyl ester
• 英文别名: 2-oxo-piperidine-1-carboxylic acid ethyl ester；Ethyl 2-oxopiperidine-1-carboxylate
• CAS: 33485-71-1
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: CMVAYPJYRXHDOB-UHFFFAOYSA-N

物化性质

• 沸点：
  181-182.5 °C(Press: 13 Torr)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-oxopiperidine-1-carboxylic acid ethyl ester 在 二甲基二环氧乙烷 、 四氯化钛 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 ethyl (2R,3S)-3-hydroxy-2-[2-oxo-3-(4-oxoquinazolin-3-yl)propyl]piperidine-1-carboxylate
  参考文献：
  名称：

  α-取代的β-羟基哌啶和吡咯烷的制备：替非福定的全合成

  摘要：

  由环状烯氨基甲酸酯产生的环氧化物是有效的N-酰基亚胺鎓离子前体，并允许制备β-羟基，α-取代的哌啶和吡咯烷。还描述了外消旋的非布利福宁的总合成。

  DOI：

  10.1016/0040-4039(96)00527-8
• 作为产物：
  描述：

  1-哌啶羧酸乙酯 在 ruthenium(IV) oxide 、 sodium chloride 作用下， 以 水 、 丙酮 为溶剂， 以89%的产率得到2-oxopiperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  INDIRECT ELECTROOXIDATION OFN-PROTECTED AMINES TO AMIDES WITH A DOUBLE MEDIATORY SYSTEM CONSISTING OF RuO₄, AND Cl⁺

  摘要：

  在饱和NaCl-丙酮体系中，利用RuO4对N-保护脂肪胺进行间接电氧化转化，可以高产率地得到相应的酰胺。

  DOI：

  10.1246/cl.1984.1063

文献信息

• Novel N-acylated heterocycles
  申请人：Recordati S.A.

  公开号：US20030162777A1

  公开（公告）日：2003-08-28

  Described are compositions comprising a muscarinic receptor antagonist and an N-acylated heterocycle derivative having affinity for serotonergic receptors, and enantiomers, diastereoisomers, N-oxides, polymorphs, solvates and pharmaceutically acceptable salts thereof. The combination of a muscarinic receptor antagonist and an N-acylated heterocycle, or an enantiomer, diastereoisomer, N-oxide, polymorph, solvate or pharmaceutically acceptable salt thereof, is useful in the treatment of patients with neuromuscular dysfunction of the lower urinary tract and diseases related to 5-HT 1A receptors.

  描述了包含一种肌氨酸受体拮抗剂和一种对5-HT 1A 受体具有亲和力的N-酰化杂环衍生物的组合物，以及它们的对映体、二对映体、N-氧化物、多型体、溶剂合物和药用可接受盐。肌氨酸受体拮抗剂和N-酰化杂环，或其对映体、二对映体、N-氧化物、多型体、溶剂合物或药用可接受盐的组合，在治疗患有下尿路神经肌肉功能障碍和与5-HT 1A 受体相关疾病的患者中是有用的。
• ¹⁵N/¹⁴N Position-Specific Isotopic Analyses of Polynitrogenous Amino Acids
  作者：Gavin L. Sacks、J. Thomas Brenna

  DOI：10.1021/ac048903o

  日期：2005.2.1

  15N/14N isotope ratios are widely used to study processes and systems involving amino acids. Nitrogen isotope fractionation in biological processes occurs primarily at sites of bond-breaking and formation; the finest discrimination for “isotopic fingerprinting” and studies of isotopic fluxes is thus obtained at the position-specific level. While there are numerous reports of natural intramolecular carbon isotope variability, there are no literature reports of 15N/14N position-specific isotopic analysis (N-PSIA) of biologically relevant molecules. We report a methodology for high-precision N-PSIA of four polynitrogenous α-amino acids (asparagine, glutamine, lysine, histidine) and the first survey of natural intramolecular 15N/14N in these biomolecules. Selective liberation of N-atoms from multiple commercial standards of each parent amino acid was achieved by an appropriate enzymatic reaction or by acid hydrolysis. 15N/14N measurements were performed on N-ethoxycarbonyl ethyl ester derivatives of the parent amino acids and their analogues by gas chromatography combustion isotope ratio mass spectrometry, and the average precision for replicate injections was found to be SD(δ15N) = 0.3‰. Position-specific δ15N values of the parent amino acid were directly observed or indirectly calculated using mass balance. The average precision obtained for directly measured positions was SD(δ15N) = 0.2−0.4‰. The average precision for indirectly obtained positions was SD(δ15N) = 0.6−1.3‰ as a result of propagation of errors. Enrichment in the side chain-N with respect to the peptide-N was observed in nearly all of the amino acid sources, most notably in asparagine (average Δδside-peptide = +11‰), which may be indicative of its method of production. In some cases, it was possible to distinguish commercial sources by N-PSIA that could not be distinguished at the compound-specific level.

  15N/14N同位素比率广泛用于研究涉及氨基酸的过程和系统。生物过程中的氮同位素分馏主要发生在断裂和形成的键位置；因此，同位素指纹鉴别和同位素通量研究的最好分辨率是在特定位置的水平上获得的。虽然有许多关于天然分子内碳同位素变化的报道，但关于与生物相关的分子进行15N/14N特定位置同位素分析（N-PSIA）的文献报道尚无报道。我们报道了一种高精度的四元多氮α-氨基酸（天冬酰胺、谷氨酰胺、赖氨酸、组氨酸）N-PSIA方法，并对这些生物分子中的天然分子内15N/14N进行了首次调查。通过适当的酶反应或酸水解，实现了从每个母体氨基酸的多个商业标准中有选择性地释放氮原子。通过气相色谱燃烧同位素比质谱法对母体氨基酸及其衍生物的N-乙氧基羰基乙酯进行15N/14N测量，重复注射的平均精度为SD（δ15N）= 0.3‰。通过质量平衡直接观察或间接计算母体氨基酸的特定位置的δ15N值。直接测量位置的平均精度为SD（δ15N）= 0.2−0.4‰。间接获得位置的平均精度为SD（δ15N）= 0.6−1.3‰，这是由于误差的传播。在几乎所有的氨基酸来源中，侧链N相对于肽N的富集最为显著地出现在天冬酰胺（平均Δδ侧链-肽键= +11‰），这可能是其生产方式的指示。在某些情况下，可以通过N-PSIA区分商业来源，而无法在化合物特定水平上进行区分。
• [EN] SUBSTITUTED SULFONAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS SUBSTITUÉS DE SULFONAMIDE
  申请人：GRUENENTHAL GMBH

  公开号：WO2009124746A1

  公开（公告）日：2009-10-15

  The invention relates to substituted sulfonamide derivatives, processes for the preparation thereof, medicaments containing these compounds and the use of substituted sulfonamide derivatives for the preparation of medicaments.

  这项发明涉及替代磺胺基衍生物，其制备方法，含有这些化合物的药物以及利用替代磺胺基衍生物制备药物。
• [EN] SUBSTITUTED INDAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'INDAZOLE SUBSTITUÉS ACTIFS EN TANT QU'INHIBITEURS DE KINASES
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2010069966A1

  公开（公告）日：2010-06-24

  Substituted indazole derivatives of formula (I) and pharmaceutically acceptable salts thereof, as defined in the specification, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful in therapy in the treatment of diseases associated with a deregulated protein kinase activity, like cancer.

  公开了公式（I）的取代吲唑衍生物及其药用盐，如规范中所定义的，其制备方法和包含它们的药物组合物；本发明的化合物可能在治疗与蛋白激酶活性失调相关的疾病，如癌症方面有用。
• Heterotricyclic Himbacine Analogs as Potent, Orally Active Thrombin Receptor (Protease Activated Receptor-1) Antagonists
  作者：Mariappan V. Chelliah、Samuel Chackalamannil、Yan Xia、Keith Eagen、Martin C. Clasby、Xiaobang Gao、William Greenlee、Ho-Sam Ahn、Jacqueline Agans-Fantuzzi、George Boykow、Yunsheng Hsieh、Matthew Bryant、Jairam Palamanda、Tze-Ming Chan、David Hesk、Madhu Chintala

  DOI：10.1021/jm070704k

  日期：2007.10.1

  Pursuing our earlier efforts in the himbacine-based thrombin receptor antagonist area, we have synthesized a series of compounds that incorporate heteroatoms in the C-ring of the tricyclic motif. This effort has resulted in the identification of several potent heterocyclic analogs with excellent affinity for the thrombin receptor. Several of these compounds demonstrated robust inhibition of platelet

  遵循我们在基于组氨酸的凝血酶受体拮抗剂领域的早期努力，我们合成了一系列在三环基序的C环中掺入杂原子的化合物。这项工作已导致鉴定出几种对凝血酶受体具有优异亲和力的有效杂环类似物。这些化合物中的几种在口服给药后在食蟹猴的离体模型中显示出对血小板聚集的强烈抑制。介绍了28b（本系列的基准化合物）的详细资料，Ki为4.3 nM。