(3S,7aR)-1-hydroxy-3-(3H-imidazol-4-ylmethyl)-7a-methyldihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)dione | 1446846-30-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,7aR)-1-hydroxy-3-(3H-imidazol-4-ylmethyl)-7a-methyldihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)dione
• 英文别名: (3S,7aR)-1-hydroxy-3-(1H-imidazol-5-ylmethyl)-7a-methyl-6,7-dihydro-3H-pyrrolo[1,2-a]imidazole-2,5-dione
• CAS: 1446846-30-5
• 化学式: C₁₁H₁₄N₄O₃
• 分子量: 250.257
• InChiKey: SHGLWPZEQSTGBO-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰丙酸 、 L-组氨酰氧肟酸 以 异丙醇 为溶剂， 反应 2.0h， 以96%的产率得到(3S,7aR)-1-hydroxy-3-(3H-imidazol-4-ylmethyl)-7a-methyldihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)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

文献信息

• Enantiomerically Enriched Bicyclic Hydroxamic Acids in One Step from <font>α</font>-Aminohydroxamic Acids and Keto Acids via Cyclocondensation
  作者：Yujiro Hoshino、Masanori Oyaizu、Yoko Koyanagi、Kiyoshi Honda

  DOI：10.1080/00397911.2012.717162

  日期：2013.9.17

  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.