(S)-3-methylvaleric acid methyl ester | 39616-77-8

• 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: (S)-3-methylvaleric acid methyl ester
• 英文别名: (S)-(+)-methyl 3-methylpentanoate；S methyl-3 pentanoate de methyle；(S)-methyl 3-methylpentanoate；methyl (S)-3-methylpentanoate；(S)-3-Methylpentanoate；(S)-3-methyl-valeric acid methyl ester；methyl (3S)-3-methylpentanoate
• CAS: 39616-77-8
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: FHASOOYJUZKVFW-LURJTMIESA-N

物化性质

• 沸点：
  135.1±8.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-methylvaleric acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (S)-(+)-3-甲基-1-戊醇
  参考文献：
  名称：

  Stereoselective synthesis of belactosin C and its derivatives using a catalytic proline catalyzed crossed-aldol reaction

  摘要：

  A highly practical and concise stereoselective total synthesis of belactosin C and synthetic variants was achieved using an S-proline catalyzed crossed-aldol reaction as the key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.059
• 作为产物：
  描述：

  L-异亮氨酸 在 sodium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 乙醚 为溶剂， 生成 (S)-3-methylvaleric acid methyl ester
  参考文献：
  名称：

  鞘氨醇类似物真菌毒素伏马菌素B 1和AAL毒素T A的完整结构：侧链的绝对构型

  摘要：

  伏马菌素B 1和AAL毒素T A是鞘氨醇类似物霉菌毒素，其特征在于丙烷-1,2,3-三羧酸侧链酯化为烷基胺骨架。骨架中所有立体异构中心的绝对构型是已知的。使用手性气相色谱法，我们确定了侧链中C-3'处的绝对构型为S，从而完成了两种毒素的结构确定。

  DOI：

  10.1016/0040-4039(95)00090-y

文献信息

• [EN] 1-HETEROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A MODULATORS<br/>[FR] DÉRIVÉS DE 1-HÉTÉROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE ET LEURS UTILISATIONS À TITRE DE MODULATEURS DE PDE9A
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009121919A1

  公开（公告）日：2009-10-08

  The invention relates to novel 1,6-disubstituted pyrazolopyrimidinones, Formula (I) with Hc is a mono-, bi- or tricyclic heterocyclyl group, the ring members of which are carbon atoms and at least 1, preferably 1, 2 or 3, heteroatom(s), which are selected from the group of nitrogen, oxygen and sulphur, which is in the form of -S(O)r - with r being 0, 1 or 2, and - said heterocyclyl group is or comprises 1 non-aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member and - said heterocyclyl group is bound to the scaffold by said 1 non- aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member. According to one aspect of the invention the new compounds are for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease.

  该发明涉及新型1,6-二取代吡唑吡嘧啶酮，化学式（I），其中Hc是一个单环、双环或三环杂环基团，其环成员为碳原子和至少1个，优选1个、2个或3个来自氮、氧和硫的杂原子，其以-S(O)r-的形式存在，其中r为0、1或2，所述杂环基团是或包括1个非芳香、饱和或部分不饱和的单环环，其中至少包含1个杂原子作为环成员，所述杂环基团通过所述至少包含1个杂原子作为环成员的非芳香、饱和或部分不饱和的单环环与支架相结合。根据该发明的一个方面，新化合物用于制造药物，特别是用于治疗感知、注意力、学习或记忆缺陷相关疾病的药物。新化合物还用于制造治疗阿尔茨海默病的药物。
• On the Mechanism of Cu-Catalyzed Enantioselective Extended Conjugate Additions: A Structure-Based Approach
  作者：Tim den Hartog、Yange Huang、Martín Fañanás-Mastral、Anne Meuwese、Alena Rudolph、Manuel Pérez、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/cs501297s

  日期：2015.2.6

  The enantioselective 1,6-addition to unsaturated carbonyl compounds offers unique opportunities to study the range of selectivities one can obtain using Cu catalysis. Here, a substrate–reagent approach to obtain structural information on the mechanism of extended conjugate additions is reported. By studying the influence of several halides in the Grignard reagent and in the Cu source on the enantioselective

  对不饱和羰基化合物的1,6-对映选择性加成提供了独特的机会来研究使用Cu催化可获得的选择性范围。在这里，报道了一种底物-试剂方法来获得有关扩展缀合物加成机理的结构信息。通过研究格氏试剂和铜源中几种卤化物对对映选择性1,6-加成的影响，表明使用EtMgBr作为格氏试剂和CuI作为铜源的组合是有利的。此外，探索带有几种烷基酯的底物发现，叔丁基酯底物增强了1,6-加成中的对映异构，并允许添加BnCH 2溴化镁。还研究了具有各种吸电子基团的底物，确定酯底物最适合1,6加成。其他两项研究的重点是Me取代的烯烃底物和具有所有可能的烯烃几何形状的底物。这些研究表明，当使用α-Me底物时，在1,6-加成中空前的高对映选择性，并为1,6-加成机理提供了相关见解。最后，研究了具有三个或四个烯烃与吸电子基团共轭的底物。在此，报道了1，8-加成，其以合理的产率，区域选择性和立体选择性给出了相应的产物。结合这些研究
• Highly Efficient Copper(I) Iodide-Tolyl-BINAP-Catalyzed Asymmetric Conjugate Addition of Methylmagnesium Bromide to α,β-Unsaturated Esters
  作者：Shun-Yi Wang、Tze-Keong Lum、Shun-Jun Ji、Teck-Peng Loh

  DOI：10.1002/adsc.200700567

  日期：2008.3.25

  A highly efficient asymmetric conjugate addition of methylmagnesium bromide (MeMgBr) to α,β-unsaturated esters catalyzed by copper(I) iodide-tolyl-BNIP (CuI-Tol-BINAP) is described.

  描述了由碘化铜（I）-甲苯基-BNIP（CuI-Tol-BINAP）催化的甲基溴化镁（MeMgBr）的高效不对称共轭加成反应。
• On the Mechanism of the Copper-Catalyzed Enantioselective 1,4-Addition of Grignard Reagents to α,β-Unsaturated Carbonyl Compounds
  作者：Syuzanna R. Harutyunyan、Fernando López、Wesley R. Browne、Arkaitz Correa、Diego Peña、Ramon Badorrey、Auke Meetsma、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/ja0585634

  日期：2006.7.19

  The mechanism of the enantioselective 1,4-addition of Grignard reagents to alpha,beta-unsaturated carbonyl compounds promoted by copper complexes of chiral ferrocenyl diphosphines is explored through kinetic, spectroscopic, and electrochemical analysis. On the basis of these studies, a structure of the active catalyst is proposed. The roles of the solvent, copper halide, and the Grignard reagent have

  通过动力学、光谱和电化学分析探索了由手性二茂二膦的铜配合物促进的格氏试剂对映选择性 1,4-加成到 α、β-不饱和羰基化合物的机制。在这些研究的基础上，提出了活性催化剂的结构。已经检查了溶剂、卤化铜和格氏试剂的作用。动力学研究支持将还原消除作为涉及手性催化剂、底物和格氏试剂的限速步骤。热力学活化参数由反应速率的温度依赖性确定。讨论了假定的活性物质和反应的催化循环。
• Volatile Lactones — (5S,S)-5-Methyl-3-(methylalkyl)furan-2(5H)-ones — Identified in the Submerged Cultivation ofStreptomyces Avermitilis
  作者：Tomáš Řezanka、Karel Sigler

  DOI：10.1002/ejoc.200600343

  日期：2006.9

  Six new compounds have been identified in the volatile fractions produced during the submerged cultivation of Streptomyces avermitilis. By recording the GC/MS, GC/FTIR, CD, 1H and 13C NMR data and by performing chemical degradation experiments, these compounds were determined to be (5S,S)-5-methyl-3-(methylalkyl)furan-2(5H)-ones. Herein, the existence of volatile lactones with an anteiso structure of

  在 Streptomyces avermitilis 水下培养过程中产生的挥发性组分中已鉴定出六种新化合物。通过记录 GC/MS、GC/FTIR、CD、1H 和 13C NMR 数据并进行化学降解实验，这些化合物被确定为 (5S,S)-5-甲基-3-(甲基烷基)呋喃-2( 5H)-一个。在此，首次记录了具有侧链反异结构的挥发性内酯的存在。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)