Methyl 2-hydroxy-4-oxohexanoate | 66376-24-7

• 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
• 英文名称: Methyl 2-hydroxy-4-oxohexanoate
• CAS: 66376-24-7
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: UULUONONKIDNAX-UHFFFAOYSA-N

物化性质

• 沸点：
  271.3±20.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-hydroxy-4-oxohexanoate 在 4-二甲氨基吡啶 、 pig liver esterase 作用下， 以 吡啶 为溶剂， 反应 48.0h， 生成 Hexanoic acid, 2-hydroxy-4-oxo-, methyl ester, (S)-
  参考文献：
  名称：

  Regio - and enantioselective bioreduction of ethyl 2,4-dioxoalkanoates and γ-Keto-α-enamino esters with fermenting baker's yeast

  摘要：

  2,4-Dioxoalkanoates 1a-d and the parent compounds gamma-keto-alpha-enamino esters 2a-d are regioselectively reduced by baker's yeast to (R)-alpha-hydroxy-gamma-ketoesters 4a-d in moderate to good chemical yield and appreciable enantioselectivity. Pig liver esterase enantioselective hydrolysis of the acetyl derivatives 3a-d, easily obtained by treatment of racemic alpha-hydroxy-gamma-keto esters 4a-d, produced the optically active (S) 4a-d in good chemical (60-92%) and optical (53-92%) yield.

  DOI：

  10.1016/s0040-4039(00)78883-6
• 作为产物：
  描述：

  methyl 2,4-dioxohexanoate 在 甲醇 、 硫酸氢铵 、 potassium dihydrogenphosphate 、 baker's yeast 、 乙醇 、 葡萄糖 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 24.0h， 以46%的产率得到Methyl 2-hydroxy-4-oxohexanoate
  参考文献：
  名称：

  Regio - and enantioselective bioreduction of ethyl 2,4-dioxoalkanoates and γ-Keto-α-enamino esters with fermenting baker's yeast

  摘要：

  2,4-Dioxoalkanoates 1a-d and the parent compounds gamma-keto-alpha-enamino esters 2a-d are regioselectively reduced by baker's yeast to (R)-alpha-hydroxy-gamma-ketoesters 4a-d in moderate to good chemical yield and appreciable enantioselectivity. Pig liver esterase enantioselective hydrolysis of the acetyl derivatives 3a-d, easily obtained by treatment of racemic alpha-hydroxy-gamma-keto esters 4a-d, produced the optically active (S) 4a-d in good chemical (60-92%) and optical (53-92%) yield.

  DOI：

  10.1016/s0040-4039(00)78883-6

文献信息

• InCl3-Catalyzed direct aldol reactions of glyoxylic acid monohydrate and glyoxylates with various ketones: scope and limitations
  作者：Teck-Peng Loh、Li-Chun Feng、Lin-Li Wei

  DOI：10.1016/s0040-4020(01)00309-x

  日期：2001.5

  The direct aldol reactions of various ketones with glyoxylic acid and glyoxylates afforded the α-hydroxy acid and α-hydroxy esters in good yields and high regioselectivities.

  各种酮与乙醛酸和乙醛酸酯的直接醛醇缩合反应以良好的产率和高的区域选择性提供了α-羟基酸和α-羟基酯。
• Cobalt(II) catalysed reaction of alkenes with aliphatic aldehydes and molecular oxygen: scope and mechanism
  作者：Sonika Bhatia、T. Punniyamurthy、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4020(01)87194-5

  日期：1993.7

  prepared using Schiff's bases derived from aromatic aldehydes and amines or α-aminoesters. These complexes are versatile catalyst for the reaction between aliphatic aldehydes and various alkenes. The outcome of the reaction is controlled by the electronic nature of the alkene as the electron deficient alkenes undergo oxidative addition of aldehydes followed by dioxygen incorporation to yield 2-hydr

  可以使用衍生自芳族醛和胺或α-氨基酯的席夫碱制备各种钴（II）配合物。这些络合物是脂肪族醛与各种烯烃之间反应的通用催化剂。反应的结果受烯烃的电子性质控制，因为缺电子的烯烃经历醛的氧化加成反应，然后引入双氧生成2-羟基（酰氧基）-4-氧酸酯或腈，而未活化或富电子的烯烃则提供了相应的环氧化物。这些反应是通过自由基途径进行的，并提出了一种常见的酰基钴中间体，用于形成4和环氧化物7。
• Cobalt(II)-catalyzed reaction of aldehydes with acetic anhydride under an oxygen atmosphere: scope and mechanism
  作者：Beena Bhatia、T. Punniyamurthy、Javed Iqbal

  DOI：10.1021/jo00072a041

  日期：1993.9

  The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium. Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals. On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene. Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the corresponding anhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions. A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes. Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurrence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.
• Andersen, Soeren H.; Das, Nalin B.; Joergensen, Ruth D., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 1, p. 1 - 14
  作者：Andersen, Soeren H.、Das, Nalin B.、Joergensen, Ruth D.、Kjeldsen, Gunhild、Knudsen, Jes S.、et al.

  DOI：——

  日期：——
• Torssell,K.; Zeuthen,O., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 118 - 124
  作者：Torssell,K.、Zeuthen,O.

  DOI：——

  日期：——