methyl 2-hydroxy-4-oxopentanoate | 55134-90-2

• 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-oxopentanoate
• CAS: 55134-90-2
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: OKXRLRLJFIQMSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-oxopentanoate 在 乙酸酐 作用下， 生成 methyl 4-oxo-2-pentenoate
  参考文献：
  名称：

  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

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮酸甲酯 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30%的产率得到methyl 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

文献信息

• BIOLOGICALLY ACTIVE MACROLIDES, COMPOSITIONS, AND USES THEREOF
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Serv

  公开号：US20140243284A1

  公开（公告）日：2014-08-28

  The present invention provides a compound of the formula (I) or (II), wherein R 1 is H, alkyl, alkenyl or aryl, R 2 is H, alkyl or aryl, R 3 is H, a alkyl, alkenyl or aryl, R 4 and R 4 -R 8 are independently R 10 , C(O)R 10 or SO 2 R 10 , wherein R 10 is H, alkyl, alkenyl or aryl, and R 9 is R 9a , C(O)R 9a or SO 2 R 9a , wherein R 9a is H, alkyl, alkenyl or aryl. R 9a can be unsubstituted or substituted with one or more oxo(═O), OR 9b , OC(O)R 9b , OSO 2 R 9b , NHR 9b , NHC(O)R 9b and NHSO 2 R 9b groups. R 9b is H, alkyl, alkenyl, or aryl. R 9b can be unsubstituted or substituted with one or more groups such as oxo(═O), OR 9c , CO 2 R 9c , CO 2 R 9c and OC(O)R 9c . R 9c is H, or a unsubstituted or substituted alkyl, alkenyl or aryl. The present invention further provides a composition comprising at least one compound of the present invention and a pharmaceutically acceptable carrier, alone or in combination with at least one additional active agent. The present invention further provides a method of treating a condition treatable by the inhibition of vacuolar-type (H+)-ATPase and a method of treating cancer.

  本发明提供了公式(I)或(II)的化合物，其中R1为H、烷基、烯基或芳基，R2为H、烷基或芳基，R3为H、烷基、烯基或芳基，R4和R4-R8独立地为R10、C(O)R10或SO2R10，其中R10为H、烷基、烯基或芳基，R9为R9a、C(O)R9a或SO2R9a，其中R9a为H、烷基、烯基或芳基。R9a可以是未取代或取代的，其中取代基为氧代(═O)、OR9b、OC(O)R9b、OSO2R9b、NHR9b、NHC(O)R9b和NHSO2R9b。R9b为H、烷基、烯基或芳基。R9b可以是未取代或取代的，其中取代基为氧代(═O)、OR9c、CO2R9c、CO2R9c和OC(O)R9c。R9c为H或未取代或取代的烷基、烯基或芳基。本发明还提供了包含本发明至少一种化合物和药学上可接受的载体的组合物，单独或与至少一种其他活性剂组合使用的方法。本发明还提供了一种治疗可通过抑制液泡型(H+)-ATP酶和一种治疗癌症的方法。
• Kashutina,M.V. et al., Doklady Chemistry, 1974, vol. 218, p. 607 - 610
  作者：Kashutina,M.V. et al.

  DOI：——

  日期：——
• 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.
• SYNTHESIS OF HOMOCHIRAL 2-HYDROXY ACIDS
  申请人：Genzyme Limited

  公开号：EP0620857A1

  公开（公告）日：1994-10-26
• US5434289A
  申请人：——

  公开号：US5434289A

  公开（公告）日：1995-07-18