methyl (2-anilino-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate | 1073950-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (2-anilino-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate
• 英文别名: methyl 2-(2-(phenylamino)-3-oxoisoindol-1-yl)acetate；methyl 2-(2-anilino-3-oxo-1H-isoindol-1-yl)acetate
• CAS: 1073950-92-1
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: RWMSSYBAYWAYLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl (2-anilino-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成
  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 在 ammonium acetate 、 锌 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 methyl (2-anilino-3-oxo-2,3-dihydro-1H-isoindol-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

文献信息

• Regioselective Synthesis of <i>N</i>-Aminoisoindolones and Mono-<i>N</i>- and Di-<i>N,N</i>′-substituted Phthalazones Utilizing Hydrazine Nucleophiles in a Palladium-Catalyzed Three-Component Cascade Process
  作者：Ronald Grigg、Visuvanathar Sridharan、Mufakhrul Shah、Simon Mutton、Colin Kilner、David MacPherson、Peter Milner

  DOI：10.1021/jo800822p

  日期：2008.11.7

  A palladium-catalyzed three-component cascade process for the synthesis of isoindolone and phthalazone derivatives is reported. The cascade process involves carbonylation of an aryl iodide/Michael acceptor to give an acylpalladium species which is intercepted by a hydrazine nucleophile. Intramolecular Michael addition follows to give either N-aminoisoindolones or mono- N- and di-N,N'-phthalazones depending

  报道了钯催化的三组分级联方法，用于合成异吲哚酮和酞菁衍生物。级联过程涉及芳基碘/迈克尔受体的羰基化，以得到酰基肼类物质，其被肼亲核试剂拦截。取决于是否使用单取代或1，2-二取代的肼亲核试剂，分子内迈克尔加成随后给出N-氨基异吲哚酮或单-N-和二-N，N'-邻苯二氮酮。