1-[(1S)-1-苯基乙基]吡咯烷-2,5-二酮 | 62993-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(1S)-1-苯基乙基]吡咯烷-2,5-二酮
• 英文名称: 1-[(1S)-1-phenylethyl]pyrrolidine-2,5-dione
• 英文别名: 1-[1-phenylethyl]pyrrolidine-2,5-dione；1-((1S)-1-Phenylethyl)succinimide
• CAS: 62993-44-6
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: YTUMRJVSFMABFS-VIFPVBQESA-N

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-[(1S)-1-苯基乙基]吡咯烷-2,5-二酮 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 5-hydroxy-1-[(1S)-1-phenylethyl]pyrrolidin-2-one
  参考文献：
  名称：

  Reaction of Pentadienyltrimethylsilane with N-Acyliminium Ion Intermediates. A Convenient Route to Pentadienyl-Substituted Lactams

  摘要：

  DOI：

  10.1021/jo00100a064
• 作为产物：
  描述：

  (S)-(-)-N-(α-甲基苄基)琥珀酰胺酸 在 sodium acetate 、 乙酸酐 作用下， 反应 0.5h， 生成 1-[(1S)-1-苯基乙基]吡咯烷-2,5-二酮
  参考文献：
  名称：

  由N保护的琥珀酰亚胺方便地一锅合成多取代的吡咯

  摘要：

  由多取代的琥珀酰亚胺与Petasis试剂之间的反应形成的二烯胺产物在温和的酸性条件下进行异构化，以优异的收率（85-95％）得到多取代的吡咯。探索了这种方法的范围和局限性。

  DOI：

  10.1016/j.tetlet.2014.03.021

文献信息

• Iridium-catalyzed asymmetric addition of imides to alkenes
  作者：Kentaro Yamakawa、Kana Sakamoto、Takahiro Nishimura

  DOI：10.1039/d3cc04406h

  日期：——

  Enantioselective addition of an imide N–H bond to alkenes was realized by use of a cationic iridium catalyst. Bulky diphosphine ligands such as DTBM-segphos, DTBM-MeO-biphep, and DTBM-binap were indispensable for the reaction. A variety of styrene derivatives, allylsilanes, and norbornene were good substrates to give the corresponding chiral adducts with high enantioselectivity.

  通过使用阳离子铱催化剂，实现了酰亚胺 N-H 键与烯烃的对映选择性加成。DTBM-segphos、DTBM-MeO-biphep 和 DTBM-binap 等大体积二膦配体对于该反应是不可或缺的。各种苯乙烯衍生物、烯丙基硅烷和降冰片烯是良好的底物，可以得到具有高对映选择性的相应手性加合物。
• 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.
• Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization
  作者：Abderrahim Chihab-Eddine、Adam Daı̈ch、Abderrahim Jilale、Bernard Decroix

  DOI：10.1016/s0040-4039(00)02037-2

  日期：2001.1

  Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by pi -cationic cyclination of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective nucleophilic additions to the carbon-nitrogen double bond. 3. Chiral acyliminium ions
  作者：Richard P. Polniaszek、Stephen E. Belmont、Ramon Alvarez

  DOI：10.1021/jo00288a036

  日期：1990.1
• POLNIASZEK, RICHARD P.;BELMONT, STEPHEN E.;ALVAREZ, RAMON, J. ORG. CHEM., 55,(1990) N, C. 215-223
  作者：POLNIASZEK, RICHARD P.、BELMONT, STEPHEN E.、ALVAREZ, RAMON

  DOI：——

  日期：——