N-(2-(苯基氨基)乙基)邻苯二甲酰亚胺 | 82806-17-5

• 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: N-(2-(苯基氨基)乙基)邻苯二甲酰亚胺
• 英文名称: 2-Anilinoethylphthalimid
• 英文别名: N-(2-(phenylamino)ethyl)phthalimide；2-(2-(phenylamino)ethyl)isoindoline-1,3-dione；N-(2-anilino-ethyl)-phthalimide；N-(2-Anilino-aethyl)-phthalimid；2-(2-Anilinoethyl)isoindole-1,3-dione
• CAS: 82806-17-5
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: GFRPMYCCKLTDIM-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C(Solv: ethanol (64-17-5))
• 沸点：
  462.9±28.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-(苯基氨基)乙基)邻苯二甲酰亚胺 在 magnesium(II) perchlorate 、 甲基肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 (3R,4S)-4-[N-(2-aminoethyl)anilino]-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel (K_ATP) Openers. 5. Identification of 4-(N-Aryl)-Substituted Benzopyran Derivatives with High Selectivity

  摘要：

  This paper describes our studies aimed at the discovery of structurally distinct analogs of the cardioprotective K-ATP Opener BMS-180448 (2) with improved selectivity for the ischemic myocardium. The starting compound 6, derived from the indole analog 4, showed good cardioprotective potency and excellent selectivity compared to 2 and the first-generation K-ATP opener cromakalim (1). The structure-activity studies indicate that increasing the size of the alkyl ester leads to diminished potency as does its replacement with a variety of other groups (nitrile, methyl sulfone). Replacement of the ethyl ester of 6 with an imidazole gave the best compound 3 (BMS-191095) of this series which maintains the potency and selectivity of its predecessor 6. The results described in this publication further support that there is no correlation between vasorelaxant and cardioprotective potencies of K-ATP openers. Compound 3 is over 20- and 4000-fold more selective far the ischemic myocardium than 2 and cromakalim (1), respectively. The selectivity for the ischemic myocardium is achieved by reduction of vasorelaxant potency rather than enhancement in antiischemic potency. As for cromakalim (1) and 2, the cardioprotective effects of compound 3 are inhibited by cotreatment with the K-ATP blocker glyburide, indicating that the K-ATP Opening is involved in its mechanism of cardioprotection With its good oral bioavailability (47%) and plasma elimination half life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo.

  DOI：

  10.1021/jm9605905
• 作为产物：
  描述：

  苯酐 、 N-苯基乙二胺 以 甲苯 为溶剂， 以80%的产率得到N-(2-(苯基氨基)乙基)邻苯二甲酰亚胺
  参考文献：
  名称：

  用于由醛和酮光催化合成哌嗪的硅胺试剂

  摘要：

  已开发出用于与醛和酮进行光催化交叉偶联以形成N-未保护的哌嗪的硅胺规程（SLAP）试剂。这种促进蓝光的方法可耐受各种杂芳族，芳族和脂族醛以及结构和立体化学复杂的SLAP试剂。它提供了SnAP（锡胺方案）试剂的无锡替代品，用于合成取代的哌嗪。

  DOI：

  10.1021/acs.orglett.6b00722

文献信息

• H2-Antihistaminika, 8. Mitt. Synthese potentieller H2-Antihistaminika der Ethylendiamin-Reihe
  作者：Jürgen Herke、Walter Schunack

  DOI：10.1002/ardp.19823150713

  日期：——

  Als potentielle H2‐Antihistaminika wurden die Ethylendiaminderivate 8,9 und 13 dargestellt und auf ihre H2‐antihistaminische Wirksamkeit untersucht.

  乙二胺衍生物 8、9 和 13 被列为潜在的 H2 抗组胺药，并检查了它们的 H2 抗组胺效果。
• Fourneau; Lestrange, Bulletin de la Societe Chimique de France, 1947, p. 827,829,831
  作者：Fourneau、Lestrange

  DOI：——

  日期：——
• Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation
  作者：Armelle Cul、Adam Daïch、Bernard Decroix、Gérard Sanz、Luc Van Hijfte

  DOI：10.1016/j.tet.2004.07.107

  日期：2004.11

  Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable alpha,beta-diamine IV (or corresponding (beta-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular alpha-aza-amidoalkylation of the N-acyliminium species. Furthermore, when R-2 is an aromatic moiety a competing alpha-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Koermendy, Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 17, p. 255,261
  作者：Koermendy

  DOI：——

  日期：——
• Gabriel, Chemische Berichte, 1889, vol. 22, p. 2221
  作者：Gabriel

  DOI：——

  日期：——