ethyl 2-hydroxy-4-oxovalerate | 89941-79-7

• 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: ethyl 2-hydroxy-4-oxovalerate
• 英文别名: 2-hydroxy-4-oxo-valeric acid ethyl ester；2-Hydroxy-4-oxo-valeriansaeure-aethylester；2-Hydroxy-laevulinsaeure-aethylester；Ethyl 2-hydroxy-4-oxopentanoate
• CAS: 89941-79-7
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: KMGFCSZYXHRXSL-UHFFFAOYSA-N

物化性质

• 沸点：
  69-70 °C(Press: 0.06 Torr)
• 密度：
  1.1319 g/cm3(Temp: 13 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：

  ethyl 2-hydroxy-4-oxovalerate 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 (S)-ethyl 2-hydroxy-4-oxopentanoate
  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：

  乙酰丙酮酸乙酯 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42%的产率得到ethyl 2-hydroxy-4-oxovalerate
  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

• Diastereoselective hydrogenation of 1,3-hydroxyketones
  申请人：——

  公开号：US20040010154A1

  公开（公告）日：2004-01-15

  The invention relates to a novel process of diastereoselective hydrogenation of 1,3-hydroxyketones of formula (I) 1 wherein R, R′ and R″ are as defined in claim 1 which is carried out in a solvent in the presence of a magnesium salt, a heterogeneous platinum catalyst and optionally an oxidant.

  这项发明涉及一种新型的对1,3-羟基酮进行不对映选择性加氢的方法，其化学式为(I)，其中R、R'和R''如权利要求1所定义，在溶剂中，在存在镁盐、非均相铂催化剂和可选氧化剂的情况下进行。
• Asymmetric Hydrogenation of 2,4-Dioxo Esters: Selective Synthesis of 2-Hydroxy-4-oxo Esters and Direct Access to Chiral 2-Hydroxy-4-butyrolactones
  作者：Véronique Blandin、Jean-François Carpentier、André Mortreux

  DOI：10.1002/(sici)1099-0690(199908)1999:8<1787::aid-ejoc1787>3.0.co;2-o

  日期：1999.8

  2,4-Dioxoesters 1a–c are selectively converted into optically active 2-hydroxy-4-oxoesters 2a–c by hydrogenation with chiral rhodium-aminophosphane-phosphinite catalysts (82–88% ee) or ruthenium-bisphosphane catalysts (52–67% ee). Direct one-pot hydrogenation of 2,4-dioxoesters 1a–c to 2-hydroxy-4-butyrolactones 4a–c proceeds in high yields; catalytic activities, chemo-, dia-, and enantioselectivities

  2,4-二氧代酯 1a-c 通过手性铑-氨基膦-次膦酸催化剂（82-88% ee）或钌-双膦催化剂（52-67）的氢化反应选择性地转化为光学活性的 2-羟基-4-氧代酯 2a-c % ee）。2,4-二氧代酯 1a-c 直接一锅加氢生成 2-羟基-4-丁内酯 4a-c，收率高；催化活性、化学选择性、渗析选择性和对映选择性在很大程度上取决于底物和催化剂的性质。
• Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2<i>H</i>)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2<i>H</i>)-pyridazinones
  作者：P. G. Baraldi、A. Bigoni、B. Cacciari、C. Caldari、S. Manfredini、G. Spalluto

  DOI：10.1055/s-1994-25663

  日期：——

  An efficient method for the preparation of 6-substituted 3(2H)-pyridazinones and 6-substituted 4,5-dihydro-4-hydroxy-3(2H)-pyridazinones starting from 3,5-disubstituted 4,5-dihydroisoxazoles is described. N-O bond cleavage of the isoxazoline ring promoted by molybdenum hexacarbonyl or by catalytic hydrogenation afforded the α-hydroxy γ-keto esters 4a-f which were converted into 6-substituted 4,5-dihydro-4-hydroxy-3(2H)-pyridazinones 5a-f or 6-substituted 3(2H)-pyridazinones 6a-f on treatment with hydrazine hydrate at room temperature or reflux in high yield starting from 4a-f. The flexibility of this protocol has been demonstrated by the synthesis of the C-nucleoside 7 starting from the known β-ribofu-ranosylnitromethane 8. Moreover, an intramolecular version of this methodology has been developed to prepare the known antiulcer tricyclic 3(2H)-pyridazinone 12.

  描述了一种从3,5-二取代的4,5-二氢异噁唑出发，高效制备6-取代的3(2H)-吡嗪酮和6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮的方法。通过六羰基钼或催化氢化促进异噁唑啉环的N-O键断裂，获得了α-羟基γ-酮酯4a-f，这些酯在室温或回流条件下与水合肼反应生成6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮5a-f或6-取代的3(2H)-吡嗪酮6a-f，且收率较高。该协议的灵活性通过从已知的β-核糖硝基甲烷8合成C-核糖苷7得到了验证。此外，还开发了一种分子内版本的方法来制备已知的抗溃疡三环3(2H)-吡嗪酮12。
• Enantio- and chemoselective reduction of 2,4-diketo acid derivatives with cinchona modified Pt-catalyst—Synthesis of (R)-2-hydroxy-4-phenylbutyric acid ethyl ester
  作者：Martin Studer、Stefan Burkhardt、Adriano F. Indolese、Hans-Ulrich Blaser

  DOI：10.1039/b002538k

  日期：——

  The enantio- and chemoselective hydrogenation of several 2,4-diketo acid derivatives to the corresponding 2-hydroxy compounds with cinchona modified Pt catalysts can be carried out with chemoselectivities of >99% and enantioselectivities up to 86% (R) and 68% (S), respectively, and enrichment to >98% ee was possible for several compounds by one crystallization, opening up an efficient technical synthesis of (R)-2-hydroxy-4-phenylbutyric acid ethyl ester, a building block for several ACE inhibitors.

  在金鸡纳改性铂催化剂的作用下，多种 2,4-二酮酸衍生物可以对映和化学选择性氢化为相应的 2-羟基化合物，化学选择性大于 99%，对映选择性分别高达 86%（R）和 68%（S）、通过一次结晶，几种化合物的对映体选择性可富集到 >98% ee，从而开辟了(R)-2-羟基-4-苯基丁酸乙酯的高效技术合成途径，而(R)-2-羟基-4-苯基丁酸乙酯是几种 ACE 抑制剂的基本成分。
• Arbuzov,Yu.A.; Klimova,E.I., Journal of general chemistry of the USSR, 1962, vol. 32, # 11, p. 3606 - 3609
  作者：Arbuzov,Yu.A.、Klimova,E.I.

  DOI：——

  日期：——