(R)-methyl 2-methylbutanoate | 55449-44-0

• 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: (R)-methyl 2-methylbutanoate
• 英文别名: methyl (R)-2-methylbutanoate；(R)-2-methyl-butyric acid methyl ester；(R)-2-Methyl-buttersaeure-methylester；Methylester der (-)(R)-Methylaethylessigsaeure；2D-Methyl-buttersaeure-methylester；(+)-Methyl-α-methylbutyrat；methyl (2R)-2-methylbutanoate
• CAS: 55449-44-0
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: OCWLYWIFNDCWRZ-RXMQYKEDSA-N

物化性质

• LogP：
  1.648 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-methylbutanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 3-(R)-sec-butyl-3-hydroxy-pentane-2,4-dione
  参考文献：
  名称：

  Reactions of methoxyvinyllithium. Synthesis and rearrangement of 4-hydroxyisopyrazoles

  摘要：

  DOI：

  10.1021/jo00879a017
• 作为产物：
  描述：

  惕各酸甲酯 在 C₅₆H₃₆F₁₂FeO₁₀P₂Ru₄ 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 100.0 ℃ 、5.0 MPa 条件下， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  高效的基于簇的催化剂，用于α-不饱和羧酸的不对称加氢

  摘要：

  新簇[H 4 Ru 4（CO）10（μ-1,2-P-P）]，[H 4 Ru 4（CO）10（1,1-P-P）]和[H 4 Ru 4（CO）11（P-P）]（P-P =基于二茂铁的Josiphos或Walphos配体家族的手性二膦）已被合成并表征。11个簇的晶体和分子结构揭示了[H 4 Ru 4（CO）10（μ1,2-P-P）]簇对于Josiphos和Walphos配体是不同的。Josiphos配体以“常规”方式桥接钌四面体的金属-金属键，即两个膦部分相对于四面体的三角形面在赤道位置配位，而Walphos配体的膦部分在一轴向和一赤道位置。两种类型的配体之间的配体尺寸和配位模式的差异似乎反映在异构化的相对倾向上。在溶液中，[H 4 Ru 4（CO）10（1,1-Walphos）]团簇异构化为相应的[H 4 Ru 4（CO）10（μ1,2-Walphos）]团簇，而含Josiphos的团簇在溶液

  DOI：

  10.1002/chem.201200630

文献信息

• Heterogeneous catalytic hydrogenation of olefinic substrates by poly-NAP
  作者：Rob ter Halle、Emmanuelle Schulz、Michel Spagnol、Marc Lemaire

  DOI：10.1016/s0040-4039(00)00377-4

  日期：2000.4

  With our previously described poly-NAP, various olefinic substrates were reduced with selectivities comparable to those obtained by BINAP. For substrates which contained a methyl ester, the selectivities were higher than those observed for their carboxylic acid analogues.

  使用我们先前描述的聚-NAP，可以还原各种烯属底物，其选择性与BINAP所获得的底物相当。对于含有甲酯的底物，其选择性高于其羧酸类似物所观察到的选择性。
• METHOD FOR PRODUCING a-SUBSTITUTED CYSTEINE OR SALT THEREOF OR SYNTHETIC INTERMEDIATE OF a-SUBSTITUTED CYSTEINE
  申请人：API Corporation

  公开号：US20160083341A1

  公开（公告）日：2016-03-24

  According to the present invention, it becomes possible to perform a process for converting into an α-substituted cysteine represented by general formula (1) or a salt thereof at low cost and on an industrial scale by employing a process that is routed through a compound represented by general formula (3) to a compound represented by general formula (6). Particularly, by employing a process that is routed through a compound represented by general formula (7-2), it becomes possible to detach a tert-butyl protection group in a simple manner and to produce the compound represented by general formula (1) with high purity. Furthermore, by employing a process that is routed through tert-butylthiomethanol or a process that is routed through a compound represented by general formula (9), it becomes possible to produce a compound represented by general formula (2) without generating bischloromethylether that is an oncogenic substance. In the production of an α-substituted-D-cysteine or a salt thereof, it becomes possible to perform a process for converting the compound represented by general formula (2) into a compound represented by general formula (3S) in one step by allowing an enzyme or the like to act on the compound represented by general formula (2).

  根据本发明，通过采用经由一种化合物（通式（3）表示）到一种通式（6）表示的化合物的过程，可以以低成本和工业化规模进行将其转化为通式（1）表示的α-取代半胱氨酸或其盐的过程。特别是，通过采用经由一种通式（7-2）表示的化合物的过程，可以简单地去除叔丁基保护基，并以高纯度生产通式（1）表示的化合物。此外，通过采用经由叔丁基硫代甲醇或经由一种通式（9）表示的化合物的过程，可以生产通式（2）表示的化合物，而不产生致癌物质双氯甲醚。在生产α-取代-D-半胱氨酸或其盐时，可以通过允许酶或类似物作用于通式（2）表示的化合物，一步将其转化为通式（3S）表示的化合物。
• Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, Pheromone Components of the Male Mouse,Mus musculus
  作者：Takuya Tashiro、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l

  日期：1999.9

  Two components [2-sec-butyl-4,5-dihydrothiazole (1) and 3,4-dehydro-exo-brevicomin (2)] of a male-produced pheromone of the mouse Musmusculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction (1516) allowing the preparation

  已以光学活性形式合成了小鼠 Musmusculus 雄性产生的信息素的两种成分 [2-sec-butyl-4,5-dihydrothiazole (1) 和 3,4-dehydro-exo-brevicomin (2)]。1 的对映异构体以对映异构体纯度为大约 . 92% ee 并且发现容易外消旋。不对称二羟基化被用作关键反应（1516），允许制备（1R，5S，7R）-2与约。94% EE。
• Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake
  作者：Yanyan Zhang、Marco Alexander Fraatz、Florian Birk、Marina Rigling、Andreas Hammer、Holger Zorn

  DOI：10.1016/j.foodchem.2018.06.027

  日期：2018.11

  occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters

  在用香菇发酵的饮料中观察到高达35％的（R）-2-甲基丁酸甲酯（M2MB）。由于M2MB通常自然地以高过量的（S）-对映异构体天然存在，因此（R）-酯的来源已通过稳定的同位素标记的前体摄食研究得以阐明。（R）-2-甲基丁酸被鉴定为底物麦芽汁中的主要前体。痕量的（R）-M2MB通过转化衍生自1-异亮氨酸的不饱和次级代谢产物（三聚醛和三聚酸）而产生。令人惊讶地，香菇酯化（[R）-2-甲基丁酸更快（[R）-M2MB比相应的（小号）-对映体。同时，香菇中发生了M2MB的自发非对映选择性降解。这解释了饮料中M2MB的不同对映体比率以及2-甲基丁酸和M2MB的不同对映体比率。由于（R）-和（S）-M2MB的气味阈值存在显着差异，因此这些发现与发酵饮料的整体风味高度相关，并阐明了所报告的2-烷基支链酸和酯的对映体比例的差异在自然界。
• Optically active 2-methyl substituted acids and esters: Chiroptical properties, conformational equilibria and NMR with opticallly active shift reagents
  作者：O Korver、M van Gorkom

  DOI：10.1016/s0040-4020(01)97381-8

  日期：1974.1

  CD spectra at 25° and −185° and in various solvents are reported for 5 2-methyl substituted carboxylic acids i.e.: (R)-2-methylbutanoic acid

  报告了5种2-甲基取代的羧酸（即（R）-2-甲基丁酸）在25°和-185°以及在各种溶剂中的CD光谱