(+)(S)-methylethylacetic acid amide | 13133-74-9

• 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)-methylethylacetic acid amide
• 英文别名: (+)(S)-Methylaethylessigsaeureamid；(S)-2-Methyl-buttersaeure-amid；(+)-(S)-α-Methyl-butyramid；opt.-akt. 2-Methyl-butyramid；2L-Methyl-buttersaeure-amid；(S)-(+)-2-Methylbutyramid；(+)-(s)-2-Methyl-butanoic amide；(2S)-2-methylbutanamide
• CAS: 13133-74-9
• 化学式: C₅H₁₁NO
• 分子量: 101.148
• InChiKey: XUXJHBAJZQREDB-BYPYZUCNSA-N

物化性质

• 熔点：
  109.9-110.3 °C
• 沸点：
  232.0±8.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)(S)-methylethylacetic acid amide 在 phosphorus pentoxide 作用下， 生成 (S)-(+)-甲基丁腈
  参考文献：
  名称：

  Kenyon; Phillips; Pittman, Journal of the Chemical Society, 1935, p. 1079

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(+)-甲基丁腈 在 {Rh(OMe)(cod)}2 水 、 三环己基膦 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 (+)(S)-methylethylacetic acid amide
  参考文献：
  名称：

  Rh（I）在环境条件下催化的有机腈水合反应。

  摘要：

  DOI：

  10.1002/anie.200800366

文献信息

• Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases
  作者：S. van Pelt、M. Zhang、L. G. Otten、J. Holt、D. Y. Sorokin、F. van Rantwijk、G. W. Black、J. J. Perry、R. A. Sheldon

  DOI：10.1039/c0ob01067g

  日期：——

  In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

  在本研究中，首次对来自红假单胞菌HaA2（HaA2）、红假单胞菌CGA009（009）、豌豆根瘤菌1021（1021）和嗜碱氮裂解菌（iso2）的多种纯化钴含氮裂解酶（NHases，EC 4.2.1.84）对一系列手性腈的立体选择性进行了筛选。对于2-苯基丙腈，来自HaA2和CGA009的NHases的立体异构比大于100。相比之下，来自已知红球菌AJ270（AJ270）的含铁NHase对一系列不同α-苯基乙腈实际上没有选择性。总的来说，对于所有测试的NHases来说，似乎至少需要一个在α-位附近的大体积基团才能实现立体选择性。连接在四级碳原子上的腈基团仅勉强被接受，并且没有显示出选择性。对于药物中间体萘普生腈，AJ270和iso2的立体异构比分别为80和大于100；iso2还将3-（1-氰乙基）苯甲酸水合为相应的酰胺，立体异构比大于100。
• Stereoselective Hydrocyanation of Alkenyl Sulfoxides as a Method to Highly Enantiomerically Enriched Compounds with Tertiary and Quaternary Chiral Carbon Atoms
  作者：Jose L. García Ruano、Marta Cifuentes García、Nieves M. Laso、Ana M. Martín Castro、Jesús H. Rodríguez Ramos

  DOI：10.1002/1521-3773(20010702)40:13<2507::aid-anie2507>3.0.co;2-r

  日期：2001.7.2

  Terminal alkynes are easily transformed into enantiomerically enriched compounds containing tertiary and quaternary carbon atoms. Sulfinylation followed by reduction (or alkylation) and hydrocyanation of the resulting vinyl sulfoxides with Et2 AlCN provides nitriles bearing the chiral center, which can in turn undergo reaction to form the desired products. Tol=4-tolyl.

  末端炔烃易于转化为对映体富集的含有叔碳原子和季碳原子的化合物。进行亚磺酰化，然后进行还原（或烷基化）和用Et 2 AlCN进行生成的乙烯基亚砜的氢氰化，使腈带有手性中心，然后该腈可以进行反应以形成所需的产物。Tol = 4-甲苯基。
• The Isonitrile—Nitrile Isomerization¹
  作者：Joseph Casanova、Newton D. Werner、Ronald E. Schuster

  DOI：10.1021/jo01349a003

  日期：1966.11
• Thermal decomposition of N-nitrosohydroxylamines. VII. Retention in the combination of optically active 2-butyl-tert-butoxy radical pairs
  作者：T. Koenig、J. M. Owens

  DOI：10.1021/ja00819a074

  日期：1974.6
• Rossi,R.; Ingrosso,G., Gazzetta Chimica Italiana, 1968, vol. 98, p. 866 - 883
  作者：Rossi,R.、Ingrosso,G.

  DOI：——

  日期：——