(S)-3-ethyl-5-methoxy-5-oxopentanoic acid | 1360140-43-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-ethyl-5-methoxy-5-oxopentanoic acid
• 英文别名: methyl 3-ethylglutarate；(3S)-3-ethyl-5-methoxy-5-oxopentanoic acid
• CAS: 1360140-43-7
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: QEODCEBFTIXFKK-LURJTMIESA-N

物化性质

• 沸点：
  286.8±23.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 3-乙基戊二酸酐 在 [(nickel)2(C10H6NCHC6H3(O)2)2] 作用下， 以 氯仿 为溶剂， 反应 28.0h， 以99%的产率得到(S)-3-ethyl-5-methoxy-5-oxopentanoic acid
  参考文献：
  名称：

  Catalytic Enantioselective Desymmetrization of meso-Glutaric Anhydrides Using a Stable Ni₂-Schiff Base Catalyst

  摘要：

  We describe the desymmetrization of meso-glutaric anhydrides to chiral hemiesters using a bench-stable homodinuclear Ni-2-(Schiff base) complex as the catalyst in good to excellent yield (up to 99%) and enantioselectivity (up to 94%). Using the opposite enantiomer of the catalyst, we obtained the same yield and enantioselectivity with the opposite configuration, thereby gaining access to both hemiester enantiomers.

  DOI：

  10.1021/ol3002078

文献信息

• Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of<i>meso</i>Cyclic Anhydrides
  作者：Lin-Jie Yan、Hai-Feng Wang、Wen-Xue Chen、Yuan Tao、Kai-Jun Jin、Fen-Er Chen

  DOI：10.1002/cctc.201600228

  日期：2016.7.6

  chloramphenicol‐base‐derived thiourea organocatalysts, (1S,2R)‐12 a–f and (1R,2R)‐15 a–c, and their use in the enantioselective alcoholysis of meso‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)‐12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)‐15 a–c. This technique was used to synthesize (R)‐(−)‐baclofen

  新的氯霉素基硫脲有机催化剂（1 S，2 R）-12 a - f和（1 R，2 R）15 a - c的合成及其在介孔酸酐的对映选择性醇解中的应用描述。特别是，如果使用低负荷的（1 S，2 R）-12 a – f负载，半酯具有出色的对映选择性。使用（1 R，2 R）‐ 15 a – c几乎没有达到对映选择性。该技术用于合成（R）-（-）-baclofen。
• Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of<i>meso</i>-cyclic anhydrides
  作者：Lingjun Xu、Shuwen Han、Linjie Yan、Haifeng Wang、Haihui Peng、Fener Chen

  DOI：10.3762/bjoc.14.19

  日期：——

  possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

  研发了一系列新型的氯霉素基础酰胺有机催化剂，它们在C-1位置具有NH官能团作为单齿氢键供体，并评估了其对中环酸酐的对映选择性有机催化醇解作用。发现这些结构多样的有机催化剂在酸酐的醇解中诱导高对映选择性，并成功地用于（S）-GABOB的不对称合成。