1-cyclohexylmethylpyrrolidine-2,5-dione

• 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-cyclohexylmethylpyrrolidine-2,5-dione
• 英文别名: 1-(cyclohexylmethyl)-2,5-pyrrolidinedione；1-(Cyclohexylmethyl)pyrrolidine-2,5-dione；1-(cyclohexylmethyl)pyrrolidine-2,5-dione
• 化学式: C₁₁H₁₇NO₂
• mdl: MFCD27929249
• 分子量: 195.261
• InChiKey: PLNMJXBWNJMINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.818
• 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-cyclohexylmethylpyrrolidine-2,5-dione 、 吡嗪-2,3-二羧酸 二甲酯 在 甲醇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以13%的产率得到7-(cyclohexylmethyl)-5,9-dihydroxypyrrolo[3,4-g]quinoxaline-6,8-dione
  参考文献：
  名称：

  Design and Optimization of Tricyclic Phtalimide Analogues as Novel Inhibitors of HIV-1 Integrase

  摘要：

  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.

  DOI：

  10.1021/jm049559q
• 作为产物：
  描述：

  1,4-丁二醇 、 环己甲腈 在 [RuH2(PPh3)4] 、 sodium hydride 、 1,3-diisopropylimidazolium bromide 作用下， 以 苯 为溶剂， 反应 18.0h， 以80%的产率得到1-cyclohexylmethylpyrrolidine-2,5-dione
  参考文献：
  名称：

  使用氢转移作为底物活化策略由腈和二醇合成环状酰亚胺

  摘要：

  开发了一种从腈和二醇合成环状酰亚胺的原子经济且用途广泛的方法。该方法利用Ru催化的转移氢化反应，其中以氧化还原中性的方式将底物，二醇和腈同时活化为内酯和胺，以提供相应的环酰亚胺，其中放出H 2气体作为唯一的副产物。这种操作简单且催化合成的方法为环状酰亚胺提供了一种可持续且容易获得的途径。

  DOI：

  10.1021/ol501835t

文献信息

• 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
• 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 of Cyclic Imides from Nitriles and Diols Using Hydrogen Transfer as a Substrate-Activating Strategy
  作者：Jaewoon Kim、Soon Hyeok Hong

  DOI：10.1021/ol501835t

  日期：2014.9.5

  method for the synthesis of cyclic imides from nitriles and diols was developed. The method utilizes a Ru-catalyzed transfer-hydrogenation reaction in which the substrates, diols, and nitriles are simultaneously activated into lactones and amines in a redox-neutral manner to afford the corresponding cyclic imides with evolution of H2 gas as the sole byproduct. This operationally simple and catalytic

  开发了一种从腈和二醇合成环状酰亚胺的原子经济且用途广泛的方法。该方法利用Ru催化的转移氢化反应，其中以氧化还原中性的方式将底物，二醇和腈同时活化为内酯和胺，以提供相应的环酰亚胺，其中放出H 2气体作为唯一的副产物。这种操作简单且催化合成的方法为环状酰亚胺提供了一种可持续且容易获得的途径。