spiro<(chromanone-4)-2:5'-N,N'-dicyclohexylhydantoine> | 103062-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: spiro<(chromanone-4)-2:5'-N,N'-dicyclohexylhydantoine>
• 英文别名: 1',3'-dicyclohexylspiro[chroman-2,4'-imidazolidine]-2',4,5'-trione；1',3'-dicyclohexylspiro[3H-chromene-2,5'-imidazolidine]-2',4,4'-trione
• CAS: 103062-01-7
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: XJRFZGNYKDIYFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  spiro<(chromanone-4)-2:5'-N,N'-dicyclohexylhydantoine> 在 盐酸羟胺 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以42%的产率得到1′,3′-dicyclohexyl-3-(2′′-hydroxyphenyl)spiro[4,5-dihydroisoxazole-5,4′-imidazolidine]-2′,5′-dione
  参考文献：
  名称：

  Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles

  摘要：

  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.

  DOI：

  10.1055/s-0034-1379613
• 作为产物：
  描述：

  N,N'-二环己基碳二亚胺 以 四氢呋喃 、 乙醇 为溶剂， 反应 40.0h， 生成 spiro<(chromanone-4)-2:5'-N,N'-dicyclohexylhydantoine>
  参考文献：
  名称：

  Filliatre, Claude; Servens, Christian, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1009 - 1010

  摘要：

  DOI：

文献信息

• Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads
  作者：Oualid Talhi、José A. Fernandes、Diana C.G.A. Pinto、Filipe A. Almeida Paz、Artur S.M. Silva

  DOI：10.1016/j.tet.2013.04.111

  日期：2013.7

  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.
• FILLIATRE, C.;SERVENS, CH., J. HETEROCYCL. CHEM., 1985, 22, N 4, 1009-1010
  作者：FILLIATRE, C.、SERVENS, CH.

  DOI：——

  日期：——