(S)-2-甲基丁酸甲酯 | 10307-60-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-2-甲基丁酸甲酯
• 中文别名: D-2-甲基丁酸甲酯
• 英文名称: (S)-2-methylbutyric acid methyl ester
• 英文别名: (2S)-2-methylbutyric acid methyl ester；(S)-2-methylbutanoic acid methyl ester；(S)-2-Methylbuttersaeure-methylester；2S-methylbutyric acid methyl ester；2-methylbutyric acid methyl ester；methyl (2S)-2-methylbutanoate
• CAS: 10307-60-5
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: OCWLYWIFNDCWRZ-YFKPBYRVSA-N

物化性质

• 沸点：
  113 °C
• 密度：
  0.883
• 闪点：
  19 °C
• 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：

  (S)-2-甲基丁酸甲酯 在 乙醚 、 草酸 作用下， 生成 2,3-二甲基-2-戊烯
  参考文献：
  名称：

  Lukes; Langthaler, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 110,113

  摘要：

  DOI：
• 作为产物：
  描述：

  惕格酸 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 、 4-二甲氨基吡啶 、 次磷酸钠一水合物 、 lithium hydroxide monohydrate 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 87.5h， 生成 (S)-2-甲基丁酸甲酯
  参考文献：
  名称：

  双功能有机催化剂在α-取代的N-丙烯酸-恶唑烷二-2-酮的磺胺-迈克尔加成中的对映选择性醇盐质子化

  摘要：

  在金鸡纳生物碱衍生的硫脲的存在下，已经研究了硫醇向α-取代的N-丙烯酰基恶唑烷丁二酮的有机催化共轭加成反应，然后进行不对称质子化。使用假对映异构体奎宁/奎尼丁衍生的催化剂，两种对映体都可以以相同水平的对映体选择性获得。加成/质子化产物已转化为有用的生物活性分子。

  DOI：

  10.1021/ol202808n

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。
• Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline–Ruthenium Complex
  作者：Jing Li、Jiefeng Shen、Chao Xia、Yanzhao Wang、Delong Liu、Wanbin Zhang

  DOI：10.1021/acs.orglett.6b00748

  日期：2016.5.6

  hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX–Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to

  在5 bar H 2下，使用RuPHOX-Ru作为手性催化剂，对各种α-取代的丙烯酸进行不对称氢化，从而以高达99％的收率和99.9％ee的产率提供相应的手性α-取代的丙酸。该反应可以以克级进行，具有相对较低的催化剂负载量（最高5000 S / C），所得产物（97％，99.3％ee）可用作构建生物活性手性分子的关键中间体。该不对称方案已成功应用于二氢青蒿酸的不对称合成，这是抗疟疾药物青蒿素工业合成所需的关键中间体。
• Resin Glycosides. XV. Simonins I-V, Ether-Soluble Resin Glycosides (Jalapins) from the Roots of Ipomoea batatas (cv. Simon).
  作者：Naoki NODA、Shigenori YODA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.40.3163

  日期：——

  Five new ether-soluble resin glycosides (jalapins), simonins I-V, have been isolated from the roots of Ipomoea batatas and characterized on the bases of chemical and spectral data. Simonim I is the first example of resin glycoside with aromatic acid (trans-cinnamic acid) as a component organic acid.

  从甘薯（Ipomoea batatas）的根部分离出五种新的醚溶性树脂糖苷（jalapins），即西蒙尼糖苷I-V，并基于化学和光谱数据对其进行了表征。西蒙尼糖苷I是首个以芳香酸（反式肉桂酸）作为组分有机酸的树脂糖苷实例。
• 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。