N-(2,4-dimethoxyphenyl)-phthalimide | 19348-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2,4-dimethoxyphenyl)-phthalimide
• 英文别名: 2-(2,4-dimethoxyphenyl)-1H-isoindole-1,3(2H)-dione；2-(2,4-dimethoxyphenyl)isoindole-1,3-dione
• CAS: 19348-40-4
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: QREZBMPWHHERAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  三甲基氯硅烷 、 N-(2,4-dimethoxyphenyl)-phthalimide 在 四乙基氯化铵 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  萘醌亚胺作为近红外染料的制备

  摘要：

  N-芳基邻苯二甲酰亚胺可以通过两次电子还原和甲硅烷基化反应转化为异吲哚。与炔属二烯亲和剂的环加成反应会导致萘醌单亚胺，其在近800 nm的NIR区域显示最大吸收。

  DOI：

  10.1016/0040-4020(95)00163-3
• 作为产物：
  描述：

  苯酐 、 2,4-二甲氧基苯胺 在 溶剂黄146 作用下， 反应 5.0h， 以75.7%的产率得到N-(2,4-dimethoxyphenyl)-phthalimide
  参考文献：
  名称：

  Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted N-Phenyl Derivatives of the Phthalimide Pharmacophore

  摘要：

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.

  DOI：

  10.1021/jm990068t

文献信息

• Regioselective C(sp²)–H imidation of arenes by redox neutral visible-light photocatalysis
  作者：Manoj Kumar Ghosh、Kumari Swati Sharma、Ganesh Pandey

  DOI：10.1039/d2ob02040h

  日期：——

  neutral visible light-induced regioselective C(sp2)–H imidation of electron-rich arenes and heteroarenes using conceptually designed redox-active 1 as a source of the N-centered imidyl radical. Structurally diverse aromatic imides were obtained in moderate to good yields. This methodology has been successfully employed for the late stage imidation of complex molecules and has also been applied towards

  我们在此报道了一种氧化还原中性可见光诱导的富电子芳烃和杂芳烃的区域选择性 C(sp 2 )–H 亚胺化，使用概念设计的氧化还原活性1作为以 N 为中心的亚胺自由基的来源。以中等到良好的产率获得了结构多样的芳香族酰亚胺。该方法已成功用于复杂分子的后期酰亚胺化，也已应用于海洋天然产物 carpatamides A、B 和 D 的正式全合成。进一步表明，生成的酰亚胺可以很容易地转化为直接就地生成相应的苯胺。
• Photocatalytic C–H Activation and Amination of Arenes with Nonactivated <i>N</i>-Hydroxyphthalimides Involving Phosphine-Mediated N–O Bond Scission
  作者：Zhentao Pan、Bo Chen、Jingxi Fang、Tong Liu、Jiayao Fang、Yongmin Ma

  DOI：10.1021/acs.joc.2c01975

  日期：2022.11.4
• US3947477A
  申请人：——

  公开号：US3947477A

  公开（公告）日：1976-03-30
• Preparation of naphthoquinone imines as NIR dyes
  作者：K.-H. Hartmann、T. Troll

  DOI：10.1016/0040-4020(95)00163-3

  日期：1995.4

  N-Arylphthalimides can be converted to isoindoles by a two electron reduction and silylation. Cycloaddition with acetylenic dienophiles leads to naphthoquinonemonoimines, which show absorption maxima in the NIR region up to 800 nm.

  N-芳基邻苯二甲酰亚胺可以通过两次电子还原和甲硅烷基化反应转化为异吲哚。与炔属二烯亲和剂的环加成反应会导致萘醌单亚胺，其在近800 nm的NIR区域显示最大吸收。
• Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted <i>N</i>-Phenyl Derivatives of the Phthalimide Pharmacophore
  作者：Joseph Vamecq、Pierre Bac、Christine Herrenknecht、Pierre Maurois、Philippe Delcourt、James P. Stables

  DOI：10.1021/jm990068t

  日期：2000.4.6

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.