1',3'-diisopropylspiro[chroman-2,4'-imidazolidine]-2',4,5'-trione | 1440420-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1',3'-diisopropylspiro[chroman-2,4'-imidazolidine]-2',4,5'-trione
• CAS: 1440420-21-2
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: SSMOIMMEZGGLQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1',3'-diisopropylspiro[chroman-2,4'-imidazolidine]-2',4,5'-trione 在 sodium 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以47%的产率得到(2'S,5R)-1,3-diisopropyl-5-(3-oxo-2,3-dihydrobenzo-furan-2-yl)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
• 作为产物：
  描述：

  色酮-2-甲酸 、 N,N'-二异丙基碳二亚胺 在 4-吡咯烷基吡啶 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到1',3'-diisopropylspiro[chroman-2,4'-imidazolidine]-2',4,5'-trione
  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

文献信息

• Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
  作者：Oualid Talhi、Artur Silva、Diana Pinto、Filipe Almeida Paz、Maamar Hamdi

  DOI：10.1055/s-0034-1379613

  日期：——

  A facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.