ethyl 2-(3-oxo-2-(phenylamino)isoindolin-1-ylidene)acetate | 1372401-29-0

• 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: ethyl 2-(3-oxo-2-(phenylamino)isoindolin-1-ylidene)acetate
• 英文别名: ethyl (2E)-2-(2-anilino-3-oxoisoindol-1-ylidene)acetate
• CAS: 1372401-29-0
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: XMPXHJBXJRTJDU-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-oxo-2-(phenylamino)isoindolin-1-ylidene)acetate 在 ammonium acetate 、 锌 作用下， 以 乙醇 为溶剂， 以85%的产率得到ethyl 2-(2-(phenylamino)-3-oxoisoindol-1-yl)acetate
  参考文献：
  名称：

  Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy- and N-Anilino-1H isoindole-1,3-(2H)-diones

  摘要：

  Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in similar to 58-63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives.

  DOI：

  10.1080/00397911.2010.551170
• 作为产物：
  描述：

  2-苯胺基-2H-异吲哚-1,3-二酮 、 乙氧甲酰基亚甲基三苯基膦 以 二甲基亚砜 为溶剂， 反应 0.17h， 以85%的产率得到ethyl 2-(3-oxo-2-(phenylamino)isoindolin-1-ylidene)acetate
  参考文献：
  名称：

  Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy- and N-Anilino-1H isoindole-1,3-(2H)-diones

  摘要：

  Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in similar to 58-63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives.

  DOI：

  10.1080/00397911.2010.551170

文献信息

• Regioselective Condensation of Alkylidenephosphoranes to <i>N</i>-Methoxy- and <i>N</i>-Anilino-1<i>H</i> isoindole-1,3-(2<i>H</i>)-diones
  作者：Wafaa M. Abdou、Rizk E. Khidre、Reham F. Barghash

  DOI：10.1080/00397911.2010.551170

  日期：2012.7.1

  Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in similar to 58-63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives.