2-hydroxy-4-oxo-butyric acid | 135089-53-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-hydroxy-4-oxo-butyric acid
• 英文别名: 2-Hydroxy-4-oxo-buttersaeure；2-Hydroxy-4-oxobutanoic acid
• CAS: 135089-53-1
• 化学式: C₄H₆O₄
• mdl: MFCD19229009
• 分子量: 118.089
• InChiKey: XJFSDAQUZXSRMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-oxo-butyric acid 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以80%的产率得到(±)-α-羟基-γ-丁内酯
  参考文献：
  名称：

  Synthesis of α-hydroxy-γ-butyrolactones from acrylates and 1,3-dioxolanes using N-hydroxyphthalimide (NHPI) as a key catalyst

  摘要：

  A new route to alpha-hydroxy-gamma-butyrolactones through three-component radical coupling of 1,3-dioxoranes, acrylates, and molecular oxygen using N-hydroxyphthalimide (NHPI) as a key catalyst has been developed. For example, the addition of 1,3dioxarane to methyl acrylate under dioxygen by NHPI followed by catalytic hydrogenation of the resulting adduct on Pd/C afforded alpha-hydroxy-gamma-butyrolactone in good yield. This method provides a facile approach to alpha-hydroxy-gamma-butyrolactones, which are difficult to synthesize by conventional methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.137
• 作为产物：
  描述：

  2-羟基-4-戊烯酸 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到2-hydroxy-4-oxo-butyric acid
  参考文献：
  名称：

  Fructose 1,6-Bisphosphate Aldolase fromStaphylococcus carnosus: Overexpression, Structure Prediction, Stereoselectivity, and Application in the Synthesis of Bicyclic Sugars

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1882::aid-chem1882>3.0.co;2-c

文献信息

• Boeeseken et al., Recueil des Travaux Chimiques des Pays-Bas, 1931, vol. 50, p. 1023,1024, 1026, 1033
  作者：Boeeseken et al.

  DOI：——

  日期：——
• Fructose 1,6-Bisphosphate Aldolase fromStaphylococcus carnosus: Overexpression, Structure Prediction, Stereoselectivity, and Application in the Synthesis of Bicyclic Sugars
  作者：Maria Teresa Zannetti、Christiane Walter、Marion Knorst、Wolf-Dieter Fessner

  DOI：10.1002/(sici)1521-3765(19990604)5:6<1882::aid-chem1882>3.0.co;2-c

  日期：1999.6.4
• Synthesis of α-hydroxy-γ-butyrolactones from acrylates and 1,3-dioxolanes using N-hydroxyphthalimide (NHPI) as a key catalyst
  作者：Takashi Kagayama、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/j.tetlet.2005.03.137

  日期：2005.5

  A new route to alpha-hydroxy-gamma-butyrolactones through three-component radical coupling of 1,3-dioxoranes, acrylates, and molecular oxygen using N-hydroxyphthalimide (NHPI) as a key catalyst has been developed. For example, the addition of 1,3dioxarane to methyl acrylate under dioxygen by NHPI followed by catalytic hydrogenation of the resulting adduct on Pd/C afforded alpha-hydroxy-gamma-butyrolactone in good yield. This method provides a facile approach to alpha-hydroxy-gamma-butyrolactones, which are difficult to synthesize by conventional methods. (c) 2005 Elsevier Ltd. All rights reserved.