methyl (2S)-2-hydroxy-2-methylbutanoate | 208117-20-8

• 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: methyl (2S)-2-hydroxy-2-methylbutanoate
• 英文别名: S-2-hydroxy-2-methylbutyric acid methyl ester；methyl (S)-(+)-2-hydroxy-2-methylbutyrate
• CAS: 208117-20-8
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: FMXYCZVOMYLMKM-LURJTMIESA-N

物化性质

• 沸点：
  152.1±8.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-hydroxy-2-methylbutanoate 在 吡啶 、 4-二甲氨基吡啶 、 Oxone 、 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 1,2-二氯乙烷 、 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-[(4-methylsulfonyl)phenyl]-3-oxolen-2-one
  参考文献：
  名称：

  实用的COX-2特异性抑制剂的对映选择性合成

  摘要：

  已经描述了COX-2特异性抑制剂1的两种合成策略，其允许以（S）-2-羟基-2-甲基丁酸的79％的总产率大量制备。这些研究已导致鉴定出（±）-2-羟基-2-甲基丁酸的有效拆分和新型亚硫酰氯辅助从酸6形成酰胺11的方法。

  DOI：

  10.1016/s0040-4020(02)00826-8
• 作为产物：
  描述：

  甲醇 、 R-1-naphthalen-1-yl-ethylamine salt of S-2-hydroxy-2-methylbutyric acid 在 硫酸 作用下， 反应 3.0h， 以92%的产率得到methyl (2S)-2-hydroxy-2-methylbutanoate
  参考文献：
  名称：

  [EN] FIBRATE COMPOUNDS HAVING PPAR AGONIST ACTIVITY
  [FR] COMPOSES DE FIBRATE POSSEDANT UNE ACTIVITE AGONISTE PPAR

  摘要：

  公开号：

  WO2006029075A3

文献信息

• HETEROCYCLIC INHIBITORS OF MCT4
  申请人：Vettore, LLC

  公开号：US20180162822A1

  公开（公告）日：2018-06-14

  Disclosed herein are compounds and compositions useful in the treatment of MCT4 mediated diseases, such as proliferative and inflammatory diseases, having the structure of Formula I: Methods of inhibition MCT4 activity in a human or animal subject are also provided.

  本文披露了一些化合物和组合物，适用于治疗由MCT4介导的疾病，如增殖性和炎症性疾病，其结构如下所示： 还提供了在人类或动物主体中抑制MCT4活性的方法。
• Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration
  作者：Yao-Jun Shi、David L. Hughes、James M. McNamara

  DOI：10.1016/s0040-4039(03)00728-7

  日期：2003.4

  Mitsunobu reaction of chiral tertiary alcohol (S)-2 with phenol 3 provides the desired ether (R)-1 in moderate yields at elevated temperatures (80–100°C). The SN2 displacement pathway is evident by complete inversion of the (S)-alcohol to (R)-ether.

  手性叔醇（S）-2与苯酚3的Mitsunobu反应在高温（80-100°C）下以中等收率提供所需的醚（R）-1。通过将（S）-醇完全转化为（R）-醚，可以明显看出S N 2的置换途径。
• Fibrate Compounds Having Ppar Agonist Activity
  申请人：Das Saibal Kumar

  公开号：US20080114005A1

  公开（公告）日：2008-05-15

  There are provided derivatives having PPAR agonist activity. The derivatives include compounds and/or their pharmaceutically acceptable salts; the compounds having the formula (I) wherein A has the structure (II) or (III); X is chosen from —CH 2 —, —O—, —NH—, and —S—; Y is chosen from —O—, —NH—, and —S—; Z, which may be located in any position of substitution, is hydrogen or halogen; R 1 and R 2 , which may be the same or different, are independently chosen from hydrogen and C 1 -C 8 alkyl, or R 1 and R 2 together form a carbocyclic ring having from 4 to 6 carbon atoms; R 3 is chosen from hydrogen and C 1 -C 8 alkyl; R 4 , R 5 , and R 6 , which may be the same or different, are independently chosen from hydrogen and C 1 -C 8 alkyl; and n is 1 to 6. Various embodiments and variants are provided. In accordance with other aspects, the invention also provides methods of producing a PPARα agonist activity in a mammal, the methods including administering to the mammal an effective amount of certain derivative(s) of the first aspect of the invention, a method of producing a PPARα agonist activity and a PPARα agonist activity in a mammal, the method including administering to the mammal an effective amount of certain derivative(s); and a pharmaceutical composition that includes the derivative(s) of the first aspect of the invention and one or more pharmaceutically-acceptable excipients. Various embodiments and variants are provided.

  提供了具有PPAR激动剂活性的衍生物。这些衍生物包括化合物和/或其药学上可接受的盐；其中化合物具有公式（I），其中A具有结构（II）或（III）；X选择自—CH2—，—O—，—NH—和—S—；Y选择自—O—，—NH—和—S—；Z可以位于任何取代位置，是氢或卤素；R1和R2，可以相同也可以不同，独立地选择自氢和C1-C8烷基，或者R1和R2共同形成具有4到6个碳原子的碳环；R3选择自氢和C1-C8烷基；R4，R5和R6，可以相同也可以不同，独立地选择自氢和C1-C8烷基；n为1到6。提供了各种实施例和变体。根据其他方面，本发明还提供在哺乳动物中产生PPARα激动剂活性的方法，该方法包括向哺乳动物投与某些第一方面的衍生物的有效量，一种产生PPARα激动剂活性的方法和在哺乳动物中的PPARα激动剂活性，该方法包括向哺乳动物投与某些衍生物的有效量；以及包括第一方面的衍生物和一个或多个药学上可接受的辅料的药物组合物。提供了各种实施例和变体。
• N-(ARYL/HETEROARYLACETYL) AMINO ACID ESTERS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND METHODS FOR INHIBITING BETA-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS BY USE OF SUCH COMPOUNDS
  申请人：Elan Pharmaceuticals, Inc.

  公开号：EP0951464B1

  公开（公告）日：2005-05-11
• Al-Catalyzed Enantioselective Alkylation of α-Ketoesters by Dialkylzinc Reagents. Enhancement of Enantioselectivity and Reactivity by an Achiral Lewis Base Additive
  作者：Laura C. Wieland、Hongbo Deng、Marc L. Snapper、Amir H. Hoveyda

  DOI：10.1021/ja053259w

  日期：2005.11.1

  An Al-catalyzed enantioselective method for additions of Me2Zn and Et2Zn to alpha-ketoesters bearing aromatic, alkenyl, and alkyl substituents is disclosed. Transformations are promoted in the presence of a readily available amino acid-based ligand and afford the desired products in excellent yields and in up to 95% ee. Investigations described illustrate that the presence of a Lewis basic additive can lead to significant enhancements in efficiency and enantioselectivity. A mechanistic model that provides a rationale for such effects is provided.