ethyl (E)-2-(2-methoxy-3-oxoisoindolin-1-ylidene)acetate | 1372401-17-6

• 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 (E)-2-(2-methoxy-3-oxoisoindolin-1-ylidene)acetate
• 英文别名: ethyl 2-(2-methoxy-3-oxoisoindolin-1-ylidene)acetate；ethyl (2E)-2-(2-methoxy-3-oxoisoindol-1-ylidene)acetate
• CAS: 1372401-17-6
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: JZAPVUHIUVIPOY-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  ethyl (E)-2-(2-methoxy-3-oxoisoindolin-1-ylidene)acetate 在 ammonium acetate 、 锌 作用下， 以 乙醇 为溶剂， 以80%的产率得到ethyl 2-(2-methoxy-3-oxoisoindolin-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：

  N-甲氧基邻苯二甲酰亚胺 、 乙氧甲酰基亚甲基三苯基膦 以 二甲基亚砜 为溶剂， 反应 0.13h， 以85%的产率得到ethyl (E)-2-(2-methoxy-3-oxoisoindolin-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

• Palladium(II)/Lewis Acid-Catalyzed Oxidative Olefination/Annulation of <i>N</i>-Methoxybenzamides: Identifying the Active Intermediates through NMR Characterizations
  作者：Jing-Wen Xue、Miao Zeng、Hongwu Jiang、Kaiwen Li、Zhuqi Chen、Guochuan Yin

  DOI：10.1021/acs.joc.9b03484

  日期：2020.7.17

  including an unsymmetrical η6-complex and a palladacycle species without the proton releasing to the environment, were identified through NMR characterizations. The in situ formation of the heterobimetallic Pd(II)/LA species such as Pd(II)/Sc(III) may have enhanced the electrophilic properties of the Pd2+ cation, thus improving the stability of the π-complex, herein, an unsymmetrical η6-complex, and

  尽管Pd（II）催化的芳烃中的C–H活化在有机合成中已经取得了广泛的成功，并且分离了许多PalLAdacycle化合物作为配体导向的C–H活化的中间体，但是可以直接鉴定反应中间体，例如π-络合物由于不稳定，C–H激活仍然无法成功。在本研究中，我们引入一个钯（II）/ LA（LA：路易斯酸）催化氧化烯/环之间的反应Ñ -methoxybenzamides和丙烯酸酯与氧作为氧化剂源，其中两个中间体，包括不对称的η 6通过NMR鉴定，确定了复合物和没有质子释放到环境中的palLAdacycle物种。在原位诸如Pd（II）/ Sc（III）的杂双金属Pd（II）/ LA物种的形成可能会增强Pd 2+阳离子的亲电特性，从而改善π络合物的稳定性，此处为不对称η 6-络合物，并提高其催化效率。观察到的不灵敏的电子效应更倾向于协同金属化-去质子化（CMD）机理来实现这种C-H活化，并且检测到的不存在质子释