4-(呋喃-2-基)-4-羟基-2-氧代丁酸 | 1034123-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 4-(呋喃-2-基)-4-羟基-2-氧代丁酸
• 英文名称: 4-(furan-2-yl)-4-hydroxy-2-oxobutanoic acid
• CAS: 1034123-70-0
• 化学式: C₈H₈O₅
• 分子量: 184.149
• InChiKey: LEYNHABFMNSAFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠醛 、 草酰乙酸 在 macrophomate synthase from Macrophoma commelinae 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 7.17h， 生成 4-(呋喃-2-基)-4-羟基-2-氧代丁酸 、 (3E)-4-(furan-2-yl)-2-oxobut-3-enoic acid
  参考文献：
  名称：

  The Putative Diels−Alderase Macrophomate Synthase is an Efficient Aldolase

  摘要：

  We find that the putative Diels-Alderase macrophomate synthase (MPS) catalyzes the addition of pyruvate enolate, generated by decarboxylation of oxaloacetate, to a variety of aldehydes. Alkyl, aryl, and heteroaryl aldehydes are accepted as substrates, providing gamma-hydroxy-alpha-ketoacids in 35-95% yield with modest levels of stereochemical control. These aldol products, which are difficult to synthesize by other methods, are formed with efficiency comparable to that of macrophomate. Our results thus provide evidence that a two-step Michael-aldol pathway is a plausible alternative to the postulated [4 + 2] cycloaddition in the MPS-catalyzed addition of pyruvate enolate to 2-pyrones. They are also relevant to understanding the divergent evolution of type II pyruvate aldolases.

  DOI：

  10.1021/ja8017994