N-[2-(3,5-dimethoxyphenyl)ethyl]succinimide | 1250264-79-9

• 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: N-[2-(3,5-dimethoxyphenyl)ethyl]succinimide
• 英文别名: 1-[2-(3,5-Dimethoxyphenyl)ethyl]pyrrolidine-2,5-dione；1-[2-(3,5-dimethoxyphenyl)ethyl]pyrrolidine-2,5-dione
• CAS: 1250264-79-9
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: FLXHOHFUSPDEGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(3,5-dimethoxyphenyl)ethyl]succinimide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides

  摘要：

  异吲哚异喹啉酮、吡咯异喹啉酮和苯并[a]喹嗪酮单元是通过使用 BBr3 对甲氧基取代的 N-苯乙基亚酰胺进行分子内环化而构建的。

  DOI：

  10.1039/c0ob00269k
• 作为产物：
  描述：

  丁二酸酐 、 3,5-二甲氧基苯乙胺 在 乙酰氯 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 1.5h， 以74%的产率得到N-[2-(3,5-dimethoxyphenyl)ethyl]succinimide
  参考文献：
  名称：

  An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides

  摘要：

  异吲哚异喹啉酮、吡咯异喹啉酮和苯并[a]喹嗪酮单元是通过使用 BBr3 对甲氧基取代的 N-苯乙基亚酰胺进行分子内环化而构建的。

  DOI：

  10.1039/c0ob00269k

文献信息

• Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors
  作者：Arumugam Suyavaran、Chitteti Ramamurthy、Ramachandran Mareeswaran、Yagna Viswa Shanthi、Jayaraman Selvakumar、Selvaraj Mangalaraj、Muthuvel Suresh Kumar、Chinnasamy Ramaraj Ramanathan、Chinnasamy Thirunavukkarasu

  DOI：10.1016/j.bmc.2014.12.017

  日期：2015.2

  A series of novel fused isoquinolinones with isoindoloisoquinolinone, pyroloisoquinolinone, and benzoquinalizinone skeletons were synthesized from corresponding phenethylimides. The isoquinolinone derivatives were evaluated for their protective effect on chicken erythrocytes subjected to oxidative damage. The effect of isoquinolinone derivatives were analysed by estimation of cell viability, antioxidant enzyme activities, DNA damage (comet assay), PARP-1 inhibition assay and molecular docking of the compounds with PARP-1 active site. The compounds CRR-271, CRR-288 and CRR-224+225 showed significant protective effect at 100 mu M concentration. The PARP-1 inhibition assay revealed the IC50 values of CRR-271, CRR-288 and CRR-224+225 as <200 nM, further molecular docking studies shows higher binding energies with PARP-1 active site. Interesting findings in this study suggest that the novel isoquinolinone derivatives inhibit PARP-1 activity and protect cells against oxidative DNA damage, which could be implemented in the treatment of inflammatory diseases. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Condensed Tetrahydroisoquinoline Class of Alkaloids by Employing TfOH-Mediated Imide Carbonyl Activation
  作者：Jayaraman Selvakumar、Ramana Sreenivasa Rao、Vijayan Srinivasapriyan、Srinivasan Marutheeswaran、Chinnasamy Ramaraj Ramanathan

  DOI：10.1002/ejoc.201403617

  日期：2015.4

  isoindoloisoquinolinones, pyrroloisoquinolinones, and benzo[a]quinolizinones were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. By employing this simple method, the isoquinoline alkaloids crispine A, trolline/oleracein E, and erythrinarbine were successfully synthesized in racemic form. The reaction

  通过使用 TfOH 介导的（TfOH = 三氟甲磺酸）酰亚胺羰基活化和环化策略，从相应的酰亚胺成功组装了基于异喹啉的多环内酰胺，例如异吲哚异喹啉酮、吡咯并异喹啉酮和苯并 [a] 喹啉酮。通过使用这种简单的方法，异喹啉生物碱松脆 A、三乙醇胺/油茶素 E 和红菊素以外消旋形式成功合成。不对称 N-苯乙基邻苯二甲酰亚胺与 TfOH 的反应显示出优异的区域选择性，这通过 DFT 计算得到了合理化。
• An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides
  作者：Jayaraman Selvakumar、Alexandros Makriyannis、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c0ob00269k

  日期：——

  Isoindoloisoquinalinone, pyrroloisoquinolinone and benzo[a]quinolizinone units are constructed via intramolecular cyclization of the methoxy substituted N-phenethylimides using BBr3.

  异吲哚异喹啉酮、吡咯异喹啉酮和苯并[a]喹嗪酮单元是通过使用 BBr3 对甲氧基取代的 N-苯乙基亚酰胺进行分子内环化而构建的。