N-(2-oxo-2-pyrrolidin-1-yl-ethyl)-acetamide | 144760-71-4

• 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
• 英文名称: N-(2-oxo-2-pyrrolidin-1-yl-ethyl)-acetamide
• 英文别名: N-(2-oxo-2-pyrrolidin-1-ylethyl)acetamide
• CAS: 144760-71-4
• 化学式: C₈H₁₄N₂O₂
• mdl: MFCD24388086
• 分子量: 170.211
• InChiKey: UJZAMTCFRPEEOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.6±28.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-2-pyrrolidin-1-yl-ethyl)-acetamide 在 rhodium(II) perfluorobutyroamidate 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 10.0h， 生成 7-methyl-3,5,9-trioxo-8-(2-oxo-pyrrolidin-1-yl-ethyl)-4-phenyl-10-oxa-4,8-diazatricyclo[5.2.1.0^2,6]decane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Site selectivity in the rhodium(II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects

  摘要：

  The product distribution obtained from Rh(II)-catalyzed decomposition of alpha-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated ligands, the diazoimide cyclized to produce an isomunchnone dipole whose formation could be monitored by NMR spectroscopy. Reaction of the dipole with a trapping agent such as N-phenylmaleimide resulted in the isolation of a 1,3-dipolar cycloadduct in high yield. The product distribution changed dramatically when rhodium(II)-acetate was employed as the catalyst. The products obtained from this reaction were derived from an azabicyclic epoxide intermediate. The catalyst effect can be modulated by the addition of Sc(OTf)(3) as a Lewis acid or by using nitromethane as the solvent. Changing the nature of the interacting carbonyl group had little effect on the cyclization pathways. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00479-1
• 作为产物：
  描述：

  四氢吡咯 、 N-乙酰甘氨酸 在 HSTU 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 N-(2-oxo-2-pyrrolidin-1-yl-ethyl)-acetamide
  参考文献：
  名称：

  通过对称探测酰胺的旋转轨迹

  摘要：

  肽基-脯氨酰片段的酰胺旋转是蛋白质骨架结构组织的重要因素。计算研究表明，这种旋转优先通过定义的过渡状态结构（syn / exo）进行。在这里，我们通过确定两个对称的脯氨酸类似物，内消旋和外消旋吡咯烷-2,5-二羧酸的酰胺键旋转势垒来补充计算结果。这些残基周围的旋转分别表示内消旋和外消旋非对映异构体的syn / exo – syn / exo和anti / endo – syn / exo杂合过渡态。前者的旋转势垒较低，约为9 kJ mol-1（水性介质），这表明syn / exo（顺时针）旋转优先于anti / endo（逆时针）旋转。

  DOI：

  10.1039/c7ob01421j

文献信息

• [EN] CALCIUM ION CHANNEL MODULATORS & USES THEREOF<br/>[FR] MODULATEURS DES CANAUX CALCIQUES ET LEURS UTILISATIONS
  申请人：LECTUS THERAPEUTICS LTD

  公开号：WO2009019508A1

  公开（公告）日：2009-02-12

  The present invention relates to ion channel modulators, and more particularly to compounds which inhibit the interaction between the pore-forming (α) subunits of Cav voltage-gated calcium channels and accessory (Cavβ subunit) proteins. Coumpounds are of use in the treatment and prevention of a number of diseases and conditions including pain and lower urinary tract disorders, and have the following Formula (I).

  本发明涉及离子通道调节剂，更具体地涉及抑制 Cav 电压门控钙通道的孔形成（α）亚单位与辅助（Cavβ亚单位）蛋白质之间相互作用的化合物。这些化合物可用于治疗和预防多种疾病和症状，包括疼痛和下尿路障碍，具有以下的化学式（I）。
• An Efficient Synthesis of<i>N,N</i>-Disubstituted 5-Aminooxazoles
  作者：Roman Mazurkiewicz

  DOI：10.1055/s-1992-26270

  日期：——

  N,N-Disubstituted 5-aminooxazoles including 4-unsubstituted derivatives, were prepared from the corresponding α-acylamino amides by treatment with dibromotriphenylphosphorane and triethylamine in refluxing dichloromethane in a novel, convenient and efficient one-pot procedure.

  N,N-二取代的5-氨基噁唑，包括4-未取代的衍生物，通过一种新颖、便捷且高效的单锅法工艺，从相应的α-酰氨基酰胺出发，在回流二氯甲烷中使用二溴三苯基膦和三乙胺处理制备得到。
• [EN] BROMODOMAIN LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME<br/>[FR] LIGANDS DE BRODOMAINES CAPABLES DE SE DIMÉRISER DANS UNE SOLUTION AQUEUSE, ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：COFERON INC

  公开号：WO2013033270A2

  公开（公告）日：2013-03-07

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.
• Site selectivity in the rhodium(II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects
  作者：Michael Prein、Peter J. Manley、Albert Padwa

  DOI：10.1016/s0040-4020(97)00479-1

  日期：1997.6

  The product distribution obtained from Rh(II)-catalyzed decomposition of alpha-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated ligands, the diazoimide cyclized to produce an isomunchnone dipole whose formation could be monitored by NMR spectroscopy. Reaction of the dipole with a trapping agent such as N-phenylmaleimide resulted in the isolation of a 1,3-dipolar cycloadduct in high yield. The product distribution changed dramatically when rhodium(II)-acetate was employed as the catalyst. The products obtained from this reaction were derived from an azabicyclic epoxide intermediate. The catalyst effect can be modulated by the addition of Sc(OTf)(3) as a Lewis acid or by using nitromethane as the solvent. Changing the nature of the interacting carbonyl group had little effect on the cyclization pathways. (C) 1997 Elsevier Science Ltd.
• Amide rotation trajectories probed by symmetry
  作者：Vladimir Kubyshkin、Nediljko Budisa

  DOI：10.1039/c7ob01421j

  日期：——

  pyrrolidine-2,5-dicarboxylic acid. The rotations around these residues represent syn/exo – syn/exo and anti/endo – syn/exo hybrid transition states for the meso and racemic diastereomer, respectively. The rotation barriers are lower for the former rotation by about 9 kJ mol−1 (aqueous medium), suggesting a strong preference for the syn/exo (clockwise) rotation over the anti/endo (anticlockwise). The

  肽基-脯氨酰片段的酰胺旋转是蛋白质骨架结构组织的重要因素。计算研究表明，这种旋转优先通过定义的过渡状态结构（syn / exo）进行。在这里，我们通过确定两个对称的脯氨酸类似物，内消旋和外消旋吡咯烷-2,5-二羧酸的酰胺键旋转势垒来补充计算结果。这些残基周围的旋转分别表示内消旋和外消旋非对映异构体的syn / exo – syn / exo和anti / endo – syn / exo杂合过渡态。前者的旋转势垒较低，约为9 kJ mol-1（水性介质），这表明syn / exo（顺时针）旋转优先于anti / endo（逆时针）旋转。