(2S)-2-hydroxy-4-methylsulfanylbutanenitrile | 948029-42-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-2-hydroxy-4-methylsulfanylbutanenitrile
• CAS: 948029-42-3
• 化学式: C₅H₉NOS
• 分子量: 131.199
• InChiKey: VWWOJJANXYSACS-YFKPBYRVSA-N

物化性质

• 沸点：
  279.6±25.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲硫基丙醛 、 丙酮氰醇 生成 (R)-2-Hydroxy-4-methylsulfanyl-butyronitrile 、 (2S)-2-hydroxy-4-methylsulfanylbutanenitrile
  参考文献：
  名称：

  Asymmetric Amino Acid Synthesis: Mitsunobu Reaction on Chiral Cyanohydrins

  摘要：

  BOC(SES)NH与手性氰醇在Mitsunobu反应条件下反应，得到了产率良好的保护α-氨基腈，这些产物随后被转化成手性氨基酸和亚氨基酸。

  DOI：

  10.1055/s-1997-6139

文献信息

• Preparation of chiral cyanohydrins by an oxynitrilase-mediated transcyanation
  作者：Vassil I. Ognyanov、Violeta K. Datcheva、Keith S. Kyler

  DOI：10.1021/ja00018a042

  日期：1991.8

  The transcyanation of aromatic and aliphatic aldehydes 1 (RCHO) with acetone cyanohydrin is catalyzed by the enzyme D-oxynitrilase to afford (R)-cyanohydrins 2 (RCH(OH)CN). The biocatalytic method using acetone cyanohydrin gives products of high enantiomeric purity with better consistency than similar conditions using hydrogen cyanide as the cyanide source. The use of an ether-buffer biphasic solvent system is essential for producing products of optimum optical purity, but the solubility properties of the substrate have a pronounced effect on the enantiomeric purity of the final product. A discussion relating the solubility partition coefficient (log P) of a substrate to the enantiomeric purity of the product as a guide for predicting the outcome with new substrates is presented. Application of the method to the preparation of the following cyanohydrins is reported (R, ee): a, C6H5, 92% ee; b, 3,4-(CH2O2)C6H3, 90% ee; c, 2-(CH3O)C6H4, 96% ee; d, C6H5CH2, 88% ee; e, CH3SCH2CH2, 92% ee; f, CH3(CH2)5CH2, 92% ee; g, (CH3)3C, 92% ee; h, c-C6H11, 96% ee; i, CH3O2C(CH2)6CH2, 97% ee; j, (E,E)-CH3CH = CHCH = CH, 96% ee; k, (CH3)2C = CHCH2CH2C(CH3) = CH, 99% ee.
• Effenberger, Franz; Ziegler, Thomas; Foerster, Siegfried, Angewandte Chemie, 1987, vol. 99, # 5, p. 491 - 492
  作者：Effenberger, Franz、Ziegler, Thomas、Foerster, Siegfried

  DOI：——

  日期：——