1-benzyl-5-oxopyrrolidine-2-carbonyl chloride | 135350-26-4

• 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: 1-benzyl-5-oxopyrrolidine-2-carbonyl chloride
• 英文别名: N-benzylpyroglutamic acid chloride；1-Benzyl-5-oxo-pyrrolidine-2-carbonylchloride
• CAS: 135350-26-4
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: LCTWWLWBABTHST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-oxopyrrolidine-2-carbonyl chloride 在 三氯化铝 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.58h， 生成 10a-cyanoethyl-1,2,3,5,10,10a-hexahydrobenzindolizine-3,10-dione
  参考文献：
  名称：

  Rigo, Benoit; Kolocouris, Nicolas, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 893 - 898

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氧代吡咯烷-2-羧酸乙酯 在 氯化亚砜 、 sodium hydride 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 29.5h， 生成 1-benzyl-5-oxopyrrolidine-2-carbonyl chloride
  参考文献：
  名称：

  Design, syntheses, and pharmacological characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan analogues as opioid receptor ligands

  摘要：

  A series of 17-cyclopropylmethyl-3,14 beta-dihydroxy-4,5 alpha-epoxy-6 alpha-(isoquinoline-3 '-carboxamido)morphinan (NAQ) analogues were synthesized and pharmacologically characterized to study their structure-activity relationship at the mu opioid receptor (MOR). The competition binding assay showed two-atom spacer and aromatic side chain were optimal for MOR selectivity. Meanwhile, substitutions at the 1 '- and/or 4 '-position of the isoquinoline ring retained or improved MOR selectivity over the kappa opioid receptor while still possessing above 20-fold MOR selectivity over the delta opioid receptor. In contrast, substitutions at the 6 '- and/or 7 '-position of the isoquinoline ring reduced MOR selectivity as well as MOR efficacy. Among this series of ligands, compound 11 acted as an antagonist when challenged with morphine in warm-water tail immersion assay and produced less significant withdrawal symptoms compared to naltrexone in morphine-pelleted mice. Compound 11 also antagonized the intracellular Ca2+ increase induced by DAMGO. Molecular dynamics simulation studies of 11 in three opioid receptors indicated orientation of the 6 '-nitro group varied significantly in the different 'address' domains of the receptors and played a crucial role in the observed binding affinities and selectivity. Collectively, the current findings provide valuable insights for future development of NAQ-based MOR selective ligands. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.02.055

文献信息

• Exploiting the regioselectivity of pyroglutamate alkylations for the synthesis of 6-azabicyclo[3.2.1]octanes and 4-azabicyclo[3.3.0]octanes
  作者：Kurt G.R. Masschelein、Christian V. Stevens、Nicolai Dieltiens、Diederica D. Claeys

  DOI：10.1016/j.tet.2007.03.084

  日期：2007.5

  Depending on the N-protecting group of pyroglutamates, the reactivity can be directed to the formation of 6-azabicyclo[3.2.1]octanes or 4-azabicyclo[3.3.0]octanes, which are conformationally restricted glutamate analogues.

  取决于焦谷氨酸的N-保护基团，反应性可被导向形成构象受限的谷氨酸类似物的6-氮杂双环[3.2.1]辛烷或4-氮杂双环[3.3.0]辛烷。
• A Convenient Method for the Conversion of a Carboxy Group into a 4,6-Di­methoxy-1,3,5-triazine Group: Application to <i>N</i>-Benzylpyroglutamic Acids
  作者：Philippe Gautret、Souhila Oudir、Benoît Rigo、Jean-Pierre Hénichart

  DOI：10.1055/s-2006-942519

  日期：2006.9

  Reaction of an activated form of carboxylic acids with a stoichiometric amount of zinc dimethyl imidodicarbonimidate (in CH2Cl2-pyridine with molecular sieves), led to 4,6-dimethoxy-1,3,5-triazines in high yields. This method has been applied to N-benzylpyroglutamic acids, in the preparation of potential antifungal products.

  将活化形式的羧酸与一定量的二甲基亚氨基二甲酰亚胺锌（在带有分子筛的 CH2Cl2 吡啶中）反应，可以高产率地制备出 4,6-二甲氧基-1,3,5-三嗪。这种方法已被应用于 N-苄基焦谷氨酸，以制备潜在的抗真菌产品。
• Studies on Pyrrolidinones. A New Rearrangement of Pyrrolo[1,2-b]Isoquinolines Derivatives
  作者：Benoît Rigo、Didier Barbry、Daniel Couturier

  DOI：10.1080/00397919108019753

  日期：1991.3

  Abstract New lactones are obtained as by-products during the Friedel-Crafts cyclization of N-arylmethyl pyroglutamoyl chlorides. A mechanism based on N-acyliminium salts is proposed to explain their formation.

  摘要 在N-芳甲基焦谷氨酰氯的Friedel-Crafts环化过程中，副产物得到了新的内酯。提出了一种基于 N-acyliminium 盐的机制来解释它们的形成。
• Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents
  作者：Shikai Zhao、Jeremiah P. Freeman、C.L. Bacon、G.B. Fox、E. O'Driscoll、A.G. Foley、J. Kelly、U. Farrell、Ciaran Regan、Stephen A. Mizsak、Jacob Szmuszkovicz

  DOI：10.1016/s0968-0896(99)00079-6

  日期：1999.8

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.
• RIGO, BENOIT;BARBRY, DIDIER;COUTURIER, DANIEL, SYNTH. COMMUN., 21,(1991) N, C. 741-747
  作者：RIGO, BENOIT、BARBRY, DIDIER、COUTURIER, DANIEL

  DOI：——

  日期：——