dimethyl (2E,3E)-2-[(dimethylamino)methylene]-3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-ylidene)butanedioate | 1158718-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: dimethyl (2E,3E)-2-[(dimethylamino)methylene]-3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-ylidene)butanedioate
• 英文别名: dimethyl (2E,3E)-2-(dimethylaminomethylidene)-3-(5-oxo-1-phenyl-2-sulfanylideneimidazolidin-4-ylidene)butanedioate
• CAS: 1158718-80-9
• 化学式: C₁₈H₁₉N₃O₅S
• 分子量: 389.432
• InChiKey: DQGBAOQLJIPQKU-HBKPYOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 (5Z)-5-[(二甲氨基)亚甲基]-3-苯基-2-硫代咪唑烷-4-酮 以 乙腈 为溶剂， 反应 2.0h， 生成 dimethyl (2E,3Z)-2-[(dimethylamino)methylene]-3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-ylidene)butanedioate 、 dimethyl (2E,3E)-2-[(dimethylamino)methylene]-3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-ylidene)butanedioate
  参考文献：
  名称：

  [2 + 2]贫电子乙炔与（5 Z）-5-[（二甲氨基）亚甲基]咪唑烷-2,4-二酮的环加成反应

  摘要：

  Abstractmagnified imageMicrowave‐assisted [2+2] cycloadditions of acetylene mono‐ and acetylenedicarboxylates 2 to (5Z)‐5‐[(dimethylamino)methylene]imidazolidine‐2,4‐dione 4a or to the corresponding thioxo derivative 4b in MeCN furnished the highly functionalized imidazolidine‐2,4‐dione derivatives 5 and 6 or the corresponding thioxo derivatives 5–7 as single isomers or mixtures of two isomers (Schemes 2 and 3, Table 1). When the reaction of (5Z)‐5‐[(dimethylamino)methylene]imidazolidine‐2,4‐dione (4c) with acetylenedicarboxylate 2a was performed in DMF, hydrolysis of the (dimethylamino)methylene group took place to give (2E)‐2‐(2,5‐dioxoimidazolidin‐4‐ylidene)butanedioate 11 (Scheme 5).

  DOI：

  10.1002/hlca.200800297

文献信息

• [2+2] Cycloadditions of Electron-Poor Acetylenes to (5<i>Z</i>)-5-[(Dimethylamino)methylene]imidazolidine-2,4-diones
  作者：Uroš Uršič、Uroš Grošelj、Anton Meden、Jurij Svete、Branko Stanovnik

  DOI：10.1002/hlca.200800297

  日期：2009.3

  Abstractmagnified imageMicrowave‐assisted [2+2] cycloadditions of acetylene mono‐ and acetylenedicarboxylates 2 to (5Z)‐5‐[(dimethylamino)methylene]imidazolidine‐2,4‐dione 4a or to the corresponding thioxo derivative 4b in MeCN furnished the highly functionalized imidazolidine‐2,4‐dione derivatives 5 and 6 or the corresponding thioxo derivatives 5–7 as single isomers or mixtures of two isomers (Schemes 2 and 3, Table 1). When the reaction of (5Z)‐5‐[(dimethylamino)methylene]imidazolidine‐2,4‐dione (4c) with acetylenedicarboxylate 2a was performed in DMF, hydrolysis of the (dimethylamino)methylene group took place to give (2E)‐2‐(2,5‐dioxoimidazolidin‐4‐ylidene)butanedioate 11 (Scheme 5).