(2R)-2-Hydroxypentanoic acid methyl ester | 96488-07-2

• 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: (2R)-2-Hydroxypentanoic acid methyl ester
• 英文别名: (R)-methyl 2-hydroxypentanoate；methyl (R)-2-hydroxypentanoate；methyl (2R)-2-hydroxypentanoate
• CAS: 96488-07-2
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: QCZPJJIXHJSOMY-RXMQYKEDSA-N

物化性质

• 沸点：
  174.2±8.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 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：

  (2R)-2-Hydroxypentanoic acid methyl ester 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-[2]naphthyloxy-valeric acid
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling Investigation of New Chiral Fibrates with PPARα and PPARγ Agonist Activity

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) are ligand-activated transcription factors that govern lipid and glucose homeostasis playing a central role in cardiovascular diseases, obesity, and diabetes. Medications targeted to PPARs have been established to treat hyper-lipidemia (fibrates) and insulin resistance (glitazones). Thus, there is significant interest in developing new and specific ligands for these receptors. Here, we present the results of the screening of new ligands of PPAR alpha and PPAR gamma. Optical isomers of new chiral fibrates were synthesized and tested in cell-based assays. Compound (S)-7 showed a dual PPARU alpha/gamma activity, and its stereochemistry was crucial in receptor activation. Protease protection experiments suggested that this compound binds directly to PPAR. Moreover, computational studies showed that it properly docks to PPAR alpha and gamma ligand binding pockets. Interestingly, (S)-7 exhibited only a modest capacity to induce the differentiation of murine fibroblasts 3T3-L1 into adipocytes compared to rosiglitazone, a well-known PPAR gamma agonist.

  DOI：

  10.1021/jm0502844
• 作为产物：
  描述：

  在 盐酸 、 钾硼氢 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 13.5h， 生成 (2R)-2-Hydroxypentanoic acid methyl ester
  参考文献：
  名称：

  Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

  摘要：

  N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00914-4

文献信息

• Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
  作者：Zechao Lin、Jiahong Li、Qingfei Huang、Qiuya Huang、Qiwei Wang、Lei Tang、Deying Gong、Jun Yang、Jin Zhu、Jingen Deng

  DOI：10.1021/acs.joc.5b00241

  日期：2015.5.1

  ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π

  设计并合成了一系列两亲性配体。具有配体的铑配合物被用于纯水中宽范围的长链脂族酮酸酯的不对称转移氢化。使用手性表面活性剂型催化剂2观察到α-，β-，γ-，δ-和ε-酮酸酯以及α-和β-酰氧基酮的定量转化率和出色的对映选择性（高达99％ee）。在金属硅油核中，催化剂与底物之间的长脂肪链之间的CH /π相互作用和长脂肪链的强疏水相互作用在催化过渡态中起着关键作用。胶束中金属催化位点与核心的疏水微环境之间的协同作用有助于实现高立体选择性。
• A simple, stereoselective synthesis of ketomethylene dipeptide isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4020(97)00410-9

  日期：1997.5

  An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.

  已经开发了一种非常简单，通用和立体选择性的方法，该方法可从Cbz保护的氨基酸和规模的2-triflyloxy酯制备酮亚甲基二肽等位异构体（5-（羰基苄氧基氨基）-2-烷基-γ-酮酸酯）。该方法是短的（三个步骤），有效的，高度非对映选择性和对映选择性的。
• Asymmetric [2,3]Wittig sigmatropic rearrangement involving a chiral azaenolate as the migrating terminus. A simple synthesis of (+)-verrucarinolactone
  作者：Kōchi Mikami、Katsuhiko Fujimoto、Takashi Kasuga、Takeshi Nakai

  DOI：10.1016/s0040-4039(01)81746-9

  日期：1984.1

  The diastereo- and/or enantioselection are described in the title rearrangement of the chiral 2-(2-alkenyloxy)methyl 2-oxazolines which eventually provides optically active α-hydroxy, γ,δ- unsaturated esters and (+)-verrucarinolactone.

  非对映异构和/或对映异构描述在手性2-（2-链烯氧基）甲基2-恶唑啉的标题重排中进行了描述，其最终提供了光学活性的α-羟基，γ，δ-不饱和酯和（+）-芦竹内酯。
• METHOD FOR SYNTHESIS OF HALOPYRIDYL-ACYCLOPENTANE DERIVATIVE AND INTERMEDIATE THEREOF
  申请人：——

  公开号：US20020010339A1

  公开（公告）日：2002-01-24

  The present invention relates to a method for synthesis of an optically active halopyridyl-azacyclo-pentane derivative and the intermediate thereof which comprises preparing an optically active allene-1,3-dicarboxylic acid ester derivative from an optically active acetonedicarboxylic acid ester derivative and then proceeding through a 7-azabicyclo[2.2.1]heptane derivative to obtain the objective product.

  本发明涉及一种合成光学活性卤代吡啶-氮杂环戊烷衍生物及其中间体的方法，包括从光学活性丙酮二羧酸酯衍生物制备光学活性联二烯-1,3-二羧酸酯衍生物，然后通过7-氮杂双环[2.2.1]庚烷衍生物进行反应，以获得目标产物。
• Inhibitors of VEGF Receptor and HGF Receptor Signaling
  申请人：Saavedra Oscar Mario

  公开号：US20100249145A1

  公开（公告）日：2010-09-30

  The invention relates to the inhibition of VEGF receptor signaling and HGF receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions

  本发明涉及抑制VEGF受体信号和HGF受体信号的技术。本发明提供了用于抑制VEGF受体信号和HGF受体信号的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和情况的组合物和方法。