succinic acid monomethylester pyrrolidine amide | 77902-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: succinic acid monomethylester pyrrolidine amide
• 英文别名: 4-oxo-4-pyrrolidino-butyric acid methyl ester；4-Oxo-4-pyrrolidino-buttersaeure-methylester；Methyl 4-oxo-4-pyrrolidin-1-ylbutanoate
• CAS: 77902-95-5
• 化学式: C₉H₁₅NO₃
• mdl: MFCD19347831
• 分子量: 185.223
• InChiKey: XQYYCGQHXUNRPK-UHFFFAOYSA-N

物化性质

• 沸点：
  161 °C(Press: 8 Torr)
• 密度：
  1.120 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 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：

  succinic acid monomethylester pyrrolidine amide 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以85%的产率得到gamma-氧代-1-吡咯烷丁酸
  参考文献：
  名称：

  Dicarboxylic Acid Azacycle l-Prolyl-pyrrolidine Amides as Prolyl Oligopeptidase Inhibitors and Three-Dimensional Quantitative Structure−Activity Relationship of the Enzyme−Inhibitor Interactions

  摘要：

  A series of dicarboxylic acid azacycle L-prolyl-pyrrolidine amides was synthesized, and their inhibitory activity against prolyl oligopeptidase (POP) from porcine brain was tested. Three different azacycles were tested at the position beyond P3 and six different dicarboxylic acids at the P3 position. L-Prolyl-pyrrolidine and L-prolyl-2(S)-cyanopyrrolidine were used at the P2-P1 positions. The IC50 values ranged from 0.39 to 19000 nM. The most potent inhibitor was the 3,3-dimethylglutaric acid azepane L-prolyl-2(S)-cyanopyrrolidine amide. Molecular docking (GOLD) was used to analyze binding interactions between different POP inhibitors of this type and the POP enzyme. The data set consisted of the novel inhibitors, inhibitors published previously by our group, and well-known reference compounds. The alignments were further analyzed using comparative molecular similarity indices analysis. The binding of the inhibitors was consistent at the P1-P3 positions. Beyond the P3 position, two different binding modes were found, one that favors lipophilic structures and one that favors nonhydrophobic structures.

  DOI：

  10.1021/jm0500020
• 作为产物：
  描述：

  gamma-氧代-1-吡咯烷丁酸 以96%的产率得到
  参考文献：
  名称：

  BLUM, Z.;EKSTROEM, M.;WISTRAND, L. -G., ACTA CHEM. SCAND., 1984, 38, N 4, 297-302

  摘要：

  DOI：

文献信息

• A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction
  作者：Christian Bellec、Olivier Gaurat

  DOI：10.1139/v04-088

  日期：2004.8.1

  Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to good yields.Key words: α-alkylated-β-ketoesters, Eschenmoser, β-enaminoesters.

  通过将硫酰胺与一种商用溴酯通过Eschenmoser缩合反应，可以方便地合成各种α-甲基-β-酮酯。通过这种硫化物收缩反应，可以轻松制备β-烯胺酯，并在中等到良好的产率下水解得到相应的β-酮酯。关键词：α-烷基化β-酮酯，Eschenmoser，β-烯胺酯。
• TMSCl Promoted Direct Conversion of Cyclic Anhydrides to (Un)Symmetric‐Diesters/Amide Esters
  作者：Meera Johny、Amuda Manikandan、Goreti Rajendar

  DOI：10.1002/asia.202301017

  日期：2024.2

  A mild, novel, and efficient silyl-promoted conversion of cyclic anhydride to diesters and amide esters. The reaction follows a two-step process, ring opening of anhydride by amine or alcohol following esterification. The reaction was carried out in the presence and absence of base. The method has broad substrate scope and is applicable for the synthesis of commercial plasticizers.

  一种温和、新颖且高效的甲硅烷基促进环酸酐向二酯和酰胺酯的转化。该反应分两步进行，酯化后通过胺或醇使酸酐开环。反应在碱存在和不存在下进行。该方法底物范围广泛，适用于商业增塑剂的合成。
• Blum, Zoltan; Ekstroem, Mikael; Wistrand, Lars-Goeran, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 4, p. 297 - 302
  作者：Blum, Zoltan、Ekstroem, Mikael、Wistrand, Lars-Goeran

  DOI：——

  日期：——
• Synthesis of 3,4-Dimethyl Spirobipyrrolidinium Salts by Cyclization of Pyrrolidinealkanols
  作者：G. E. McCASLAND、STEPHEN PROSKOW

  DOI：10.1021/jo01353a004

  日期：1957.2
• Versatile .beta.-ketoester and .beta.-ketonitrile synthesis through sulfide contraction
  作者：Kazumi Shiosaki、Gregor Fels、Henry Rapoport

  DOI：10.1021/jo00329a017

  日期：1981.7