(Z)-1,3-ditolyl-5-[3-oxobenzofuran-2(3H)-ylidene]imidazolidine-2,4-dione | 1440420-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (Z)-1,3-ditolyl-5-[3-oxobenzofuran-2(3H)-ylidene]imidazolidine-2,4-dione
• 英文别名: (5Z)-1,3-bis(4-methylphenyl)-5-(3-oxo-1-benzofuran-2-ylidene)imidazolidine-2,4-dione
• CAS: 1440420-32-5
• 化学式: C₂₅H₁₈N₂O₄
• 分子量: 410.429
• InChiKey: ZYTSLWPFHYCENJ-LNVKXUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  色酮-2-甲酸 在 碘 、 sodium 、 4-吡咯烷基吡啶 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 (Z)-1,3-ditolyl-5-[3-oxobenzofuran-2(3H)-ylidene]imidazolidine-2,4-dione 、 (E)-1,3-ditolyl-5-[3-oxobenzofuran-2(3H)-ylidene]imidazolidine-2,4-dione
  参考文献：
  名称：

  Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads

  摘要：

  a-convenient diastereoselective rearrangement of the racemic (R/S)-spirolchroman-2,4'-imidazolidine]-2',4,5'-triones 3a-c into (2'R,5S)- and (2'S,5R)-5-(3-oxo-2,3-dihydrobenzofuran-2-yl)imidazolidine-2,4-diones 4a-c under alkali conditions is described. The obtained sigma bridged benzofuran-3(2H)-one-hydantoin dyads 4a-c are subsequently transformed into pi conjugated benzofuran-3(2H)-one-hydantoin dyads 5a-c by a diastereoselective dehydrogenation using I-2 (catalytic)/DMSO system to predominantly yield the (Z)-isomer. The novel single and double bonded benzofuran-3(2H)-one-hydantoin conjugate structures 4a-c and 5a-c were unambiguously elucidated by single-crystal X-ray diffraction and 2D NMR techniques allowing an in-depth stereochemical and mechanistic discussions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.111