2-(4-甲氧基-2-甲基苯基)异吲哚-1,3-二酮 | 19348-47-1

• 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
• 中文名称: 2-(4-甲氧基-2-甲基苯基)异吲哚-1,3-二酮
• 英文名称: 2-(4-methoxy-2-methylphenyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: N-(4-methoxy-2-methylphenyl)-phthalimide；1H-Isoindole-1,3(2H)-dione, 2-(4-methoxy-2-methylphenyl)-；2-(4-methoxy-2-methylphenyl)isoindole-1,3-dione
• CAS: 19348-47-1
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: GPWWJUBKRZNKIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基-2-甲基苯基)异吲哚-1,3-二酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 过氧化氢苯甲酰 、 adogen 464 、 三苯基膦 作用下， 以 四氯化碳 、 水 、 甲苯 为溶剂， 反应 18.0h， 生成 3-methoxyisoindolo<2,1-a>quinazolin-11(5H)-one
  参考文献：
  名称：

  Guillaumel, Jean; Demerseman, Pierre, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 5, p. 1297 - 1298

  摘要：

  DOI：
• 作为产物：
  描述：

  苯酐 、 2-甲基-4-甲氧基苯胺 以 溶剂黄146 为溶剂， 以82%的产率得到2-(4-甲氧基-2-甲基苯基)异吲哚-1,3-二酮
  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

文献信息

• 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.
• 2- oder 3-Dicarbonsäureimid-Fluoranverbindungen, Verfahren zu deren Herstellung und deren Verwendung in Aufzeichnungsmaterialien
  申请人：CIBA-GEIGY AG

  公开号：EP0384895B1

  公开（公告）日：1995-12-06
• US5066814A
  申请人：——

  公开号：US5066814A

  公开（公告）日：1991-11-19
• 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。
• Guillaumel, Jean; Demerseman, Pierre, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 5, p. 1297 - 1298
  作者：Guillaumel, Jean、Demerseman, Pierre

  DOI：——

  日期：——