(3S,9bR)-3-benzyl-1-hydroxy-1,9b-dihydroimidazo[2,1-a]isoindole-2(3H),5-dione | 1446846-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3S,9bR)-3-benzyl-1-hydroxy-1,9b-dihydroimidazo[2,1-a]isoindole-2(3H),5-dione
• 英文别名: (3S,9bR)-3-benzyl-1-hydroxy-3,9b-dihydroimidazo[1,2-b]isoindole-2,5-dione
• CAS: 1446846-25-8
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: LKAGNWZJNWJIDM-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-Phenylalanine hydroxamate 、 邻羧基苯甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 20.0h， 以72%的产率得到(3S,9bR)-3-benzyl-1-hydroxy-1,9b-dihydroimidazo[2,1-a]isoindole-2(3H),5-dione
  参考文献：
  名称：

  Enantiomerically Enriched Bicyclic Hydroxamic Acids in One Step from α-Aminohydroxamic Acids and Keto Acids via Cyclocondensation

  摘要：

  New enantiomerically enriched bicyclic hydroxamic acids, 1-hydroxy-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, have been synthesized by the cyclocondensation of L--aminohydroxamic acids with keto acids in a highly chemo- and stereoselective manner. The cis configuration between the amino acid side chain and the methyl group at C7a in 1H-pyrrolo[1,2-a]imidazole-2,5-dione was unambiguously established by X-ray crystallographic analysis. This method could also be applied to the cyclocondensation with o-formylbenzoic acid, giving a tricyclic hydroxamic acid in a good yield. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717162