2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(S)-butanoic acid

• 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: 2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(S)-butanoic acid
• 英文别名: (2R)-2-[(3aS,6aR)-2,5-dioxo-3,3a,6,6a-tetrahydro-1H-imidazo[4,5-d]imidazol-4-yl]butanoic acid
• 化学式: C₈H₁₂N₄O₄
• 分子量: 228.208
• InChiKey: MFTQWNDYFASAIL-WDCZJNDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,5-二羟基四氢-2H-咪唑-2-酮 、 (2R)-2-(carbamoylamino)butanoic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 海因 、 (5S)-5-ethylimidazolidine-2,4-dione 、 2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(S)-butanoic acid 、 2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(S)-butanoic acid
  参考文献：
  名称：

  Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids

  摘要：

  The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-alpha-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined for three stereoisomers by X-ray diffraction analysis.

  DOI：

  10.1070/mc2003v013n06abeh001802

文献信息

• Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids
  作者：Angelina N. Kravchenko、Konstantin Yu. Chegaev、Il’ya E. Chikunov、Pavel A. Belyakov、Elena Yu. Maksareva、Konstantin A. Lyssenko、Oleg V. Lebedev、Nina N. Makhova

  DOI：10.1070/mc2003v013n06abeh001802

  日期：2003.1

  The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-alpha-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined for three stereoisomers by X-ray diffraction analysis.