1-phenyl-3,4-dipropylazoline-2,5-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-phenyl-3,4-dipropylazoline-2,5-dione
• 英文别名: 1-Phenyl-3,4-dipropylpyrrole-2,5-dione；1-phenyl-3,4-dipropylpyrrole-2,5-dione
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: QTKCMLPMCVIGRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-辛炔 、 一氧化碳 、 异氰酸苯酯 在 十二羰基三钌 作用下， 以 均三甲苯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 以82%的产率得到1-phenyl-3,4-dipropylazoline-2,5-dione
  参考文献：
  名称：

  Ruthenium-catalyzed [2 + 2 + 1] Cocyclization of Isocyanates, Alkynes, and CO Enables the Rapid Synthesis of Polysubstituted Maleimides

  摘要：

  Intermolecular [2 + 2 + 1] cocyclization of isocyanates, alkynes, and CO (1 atm) proceeded smoothly in the presence of a catalytic amount of Ru3(CO)12 (3.3 mol %) in mesitylene at 130 degrees C for 3 approximately 42 h to give a variety of polysubstituted maleimides in excellent yields with high selectivity. The reaction may involve an azaruthenacyclopentenone intermediate derived from oxidative cyclization of an isocyanate and an alkyne on an active ruthenium species.

  DOI：

  10.1021/ja066305g

文献信息

• An Efficient Rhodium-Catalyzed Carbonylative Annulation of Internal Alkynes and Anilines To Produce Maleimides
  作者：Fengxiang Zhu、Yahui Li、Zechao Wang、Xiao-Feng Wu

  DOI：10.1002/cctc.201601092

  日期：2016.12.19

  A selective and efficient procedure for the carbonylative synthesis of polysubstituted maleimides was developed. With rhodium as the catalyst and acetylacetone (acac) as the ligand, various desired maleimide derivatives were isolated in moderate to excellent yields with good functional group tolerance from the corresponding internal alkynes and anilines.

  开发了一种选择性高效的多取代马来酰亚胺羰基合成方法。以铑为催化剂，以乙酰丙酮（acac）为配体，从相应的内部炔烃和苯胺中分离出各种所需的马来酰亚胺衍生物，并以中等至优异的收率获得了良好的官能团耐受性。
• Ruthenium-catalyzed [2 + 2 + 1] Cocyclization of Isocyanates, Alkynes, and CO Enables the Rapid Synthesis of Polysubstituted Maleimides
  作者：Teruyuki Kondo、Masato Nomura、Yasuyuki Ura、Kenji Wada、Take-aki Mitsudo

  DOI：10.1021/ja066305g

  日期：2006.11.1

  Intermolecular [2 + 2 + 1] cocyclization of isocyanates, alkynes, and CO (1 atm) proceeded smoothly in the presence of a catalytic amount of Ru3(CO)12 (3.3 mol %) in mesitylene at 130 degrees C for 3 approximately 42 h to give a variety of polysubstituted maleimides in excellent yields with high selectivity. The reaction may involve an azaruthenacyclopentenone intermediate derived from oxidative cyclization of an isocyanate and an alkyne on an active ruthenium species.