1-[(1R)-1-phenylethyl]pyrrolidine-2,5-dione | 94054-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(1R)-1-phenylethyl]pyrrolidine-2,5-dione
• 英文别名: (R)-α-methylbenzyl succinimide；(R)-(+)-N-(1-phenylethyl)succinimide；(R)-1-(1-phenylethyl)pyrrolidin-2,5-dione；1-[(1R)-1-Phenylethyl]-2,5-pyrrolidinedione
• CAS: 94054-97-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: YTUMRJVSFMABFS-SECBINFHSA-N

物化性质

• 沸点：
  386.5±21.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 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-[(1R)-1-phenylethyl]pyrrolidine-2,5-dione 在 1-bromo-3-phenylethane 、 magnesium 作用下， 以 乙醚 为溶剂， 以84%的产率得到N-(1'-phenylethyl)-4-[1-(1'-phenylethyl)-2,5-dioxopyrrolidin-3-yl]-4-oxobutanamide
  参考文献：
  名称：

  Spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile

  摘要：

  Spiro 2-pyrrolidin-5-ones were obtained from N-substituted succinimides by a two-step procedure, involving 5- or 6-endo-trig cyclisation of N-acyliminium ion intermediates with a tethered aromatic pi-nucleophile. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00418-6
• 作为产物：
  描述：

  丁二酸酐 、 R(+)-alpha-甲基苄胺 在 乙酸酐 作用下， 生成 1-[(1R)-1-phenylethyl]pyrrolidine-2,5-dione
  参考文献：
  名称：

  涉及芳香族π-亲核试剂的N-酰基亚胺离子的新型螺环化

  摘要：

  通过两步程序从N-取代的琥珀酰亚胺中获得了几个螺2-吡咯烷基-5-酮，包括在回流的三氟乙酸中螺环化N-酰亚胺离子中间体。在所有情况下，环化均利用系留的芳香族π-亲核试剂，且闭环遵循5或6 -exo-trig途径。

  DOI：

  10.1016/0040-4039(94)88240-1

文献信息

• Synthesis and stereochemical determination of batzelladine C methyl ester
  作者：Michael Butters、Christopher D. Davies、Mark C. Elliott、Joseph Hill-Cousins、Benson M. Kariuki、Li-ling Ooi、John L. Wood、Stuart V. Wordingham

  DOI：10.1039/b914744f

  日期：——

  Batzelladine C (3) is a tricyclic guanidine alkaloid of unknown stereochemistry at one centre as well as unknown absolute stereochemistry. The two possible diastereoisomers of the methyl ester corresponding to this compound have been synthesised, permitting the relative and absolute stereochemistry of this compound to be assigned.

  Batzelladine C（3）是一个在一个中心立体化学未知的三环胍生物碱，以及一个绝对立体化学未知的三环胍生物碱。已经合成了对应于该化合物的甲酯的两种可能的非对映异构体，从而可以确定该化合物的相对和绝对立体化学。
• Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile
  作者：Patrick D. Bailey、Keith M. Morgan、David I. Smith、John M. Vernon

  DOI：10.1016/0040-4039(94)88240-1

  日期：1994.9

  Several spiro 2-pyrrolidin-5-ones were obtained by a two-step procedure from N-substituted succinimides, involving spiro cyclisation of N-acyliminium ion intermediates in refluxing trifluoroacetic acid; in all cases cyclisation utilised a tethered aromatic π-nucleophile, and ring-closure followed 5- or 6-exo-trig pathways.

  通过两步程序从N-取代的琥珀酰亚胺中获得了几个螺2-吡咯烷基-5-酮，包括在回流的三氟乙酸中螺环化N-酰亚胺离子中间体。在所有情况下，环化均利用系留的芳香族π-亲核试剂，且闭环遵循5或6 -exo-trig途径。
• Design and Optimization of Tricyclic Phtalimide Analogues as Novel Inhibitors of HIV-1 Integrase
  作者：Wim G. Verschueren、Inge Dierynck、Katie I. E. Amssoms、Lili Hu、Paul M. J. G. Boonants、Geert M. E. Pille、Frits F. D. Daeyaert、Kurt Hertogs、Dominique L. N. G. Surleraux、Piet B. T. P. Wigerinck

  DOI：10.1021/jm049559q

  日期：2005.3.1

  Human immunodeficiency virus type-1 integrase is an essential enzyme for effective viral replication and hence a valid target for the design of inhibitors. We report here on the design and synthesis of a novel series of phthalimide analogues as integrase inhibitors. The short synthetic pathway enabled us to synthesize a series of analogues with a defined structure diversity. The presence of a single carbonyl-hydroxy-aromatic nitrogen motif was shown to be essential for the enzymatic activity and this was confirmed by molecular docking studies. The enzymatically most active compound from this series is 743,4-dichlorobenzyl)-5,9dihydroxypyrrolo[3,4-g]quinoxaline-6,8-dione (151) with an IC50 value of 112 nM on the HIV-1 integrase enzyme, while ((7-(4-chlorobenzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione (15k)) showed an EC50 of 270 nM against HIV-1 in a cell-based assay.
• Solvent-Switched Manganese(I)-Catalyzed Regiodivergent Distal vs Proximal C–H Alkylation of Imidazopyridine with Maleimide
  作者：Subhendu Ghosh、Tamanna Khandelia、Bhisma K. Patel

  DOI：10.1021/acs.orglett.1c02536

  日期：2021.10.1
• Spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile
  作者：Patrick D Bailey、Keith M Morgan、David I Smith、John M Vernon

  DOI：10.1016/s0040-4020(03)00418-6

  日期：2003.4

  Spiro 2-pyrrolidin-5-ones were obtained from N-substituted succinimides by a two-step procedure, involving 5- or 6-endo-trig cyclisation of N-acyliminium ion intermediates with a tethered aromatic pi-nucleophile. (C) 2003 Elsevier Science Ltd. All rights reserved.