D-phenylglycine nitrile | 45789-64-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: D-phenylglycine nitrile
• 英文别名: 2-phenylglycinonitrile；(2R)-2-amino-2-phenylacetonitrile
• CAS: 45789-64-8
• 化学式: C₈H₈N₂
• 分子量: 132.165
• InChiKey: JTIHSSVKTWPPHI-QMMMGPOBSA-N

物化性质

• 熔点：
  145-146 °C (decomp)
• 沸点：
  235.8±28.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-phenylglycine nitrile 在 硫酸 作用下， 以 aq. phosphate buffer 为溶剂， 反应 22.0h， 以95.1%的产率得到左旋苯甘氨酸酰胺
  参考文献：
  名称：

  Stereoretentive Nitrile Hydratase-Catalysed Hydration of d-Phenylglycine Nitrile

  摘要：

  The hydration of D-phenylglycine nitrile to the corresponding amide, mediated by nitrile hydratase-containing microorganisms, was studied, Batch and fed-batch reactions were compared with regard to degradation and racemisation of the chemically labile substrate. A batch process gave satisfactory results and at up to 25 mM D-phenylglycine nitrile (D-1), D-phenylglycine amide was obtained in 94% yield with 92% ee using an immobilised Rhodococcus sp. (NOVO SP 361). The enzyme could be reused, although it slowly lost its activity. When the concentration of D-phenylglycine nitrile was increased to 100 mM in a batch reaction rapid decomposition of the substrate was observed and D-phenylglycine amide was obtained in only 37% yield. A fed-batch reaction afforded an improved yield, although the decomposition of the substrate could not be avoided completely. Lowering the temperature stabilised the substrate, and a fed-batch reaction at 5 degrees C resulted in a 96% yield of D-phenylglycine amide with 95% ee. A number of other whole-cell hydratase/amidase systems also hydrated D-1 in nearly quantitative yield and >91% ee, Moreover, the ee was further increased to <99% upon prolonged reaction times with minimal loss in yield due to the action of the L-specific amidase that is present in these biocatalysts.

  DOI：

  10.1021/op000055l
• 作为产物：
  描述：

  2-amino-2-phenylacetonitrile 在 recombinant sphingomonas wittichii RW₁ nitrilase 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以68%的产率得到D-phenylglycine nitrile
  参考文献：
  名称：

  1-辛醇水溶液双相系统中腈水解酶介导的动态动力学拆分高产合成d-苯基甘氨酸及其衍生物

  摘要：

  使用1-辛醇水溶液双相系统，开发了一种腈水解酶介导的动态动力学拆分策略，用于合成d-苯基甘氨酸。由于有效抑制了苯基甘氨腈的分解，因此最大收率达81％。该结果表明腈水解酶介导的动态动力学拆分是合成d-苯基甘氨酸及其衍生物的有前途的方法。

  DOI：

  10.1016/j.tetlet.2014.01.044

文献信息

• A convenient method for optical resolutions via diastereoisomeric salt formation
  作者：M. Ács、E. Fogassy、F. Faigl

  DOI：10.1016/s0040-4020(01)96641-4

  日期：1985.1

  With the advantage of the method using two immiscrible solvents and half - equivalent amount of the resolving agent, higher optical purity can be obtained than in cases of any other resolution via diastereoisomeric salt formation, besides it is a faster procedure for resolution of a new racemate as well.

  利用使用两种不混溶的溶剂和等当量量的拆分剂的方法的优势，与通过非对映异构体盐形成而获得任何其他拆分方法相比，可以获得更高的光学纯度，此外，这是拆分新外消旋体的更快程序也一样
• Process Optimisation Studies and Aminonitrile Substrate Evaluation of <i>Rhodococcus erythropolis</i> SET1, A Nitrile Hydrolyzing Bacterium
  作者：Tatenda M. Mareya、Tracey M. Coady、Catherine O'Reilly、Michael Kinsella、Lee Coffey、Claire M. Lennon

  DOI：10.1002/open.202000088

  日期：2020.4

  enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo‐aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β‐aminonitriles, structural analogues of β‐hydroxynitriles was also investigated

  在具有底物3-羟基丁腈的腈水解红球菌SET1的腈水解反应中，完成了一系列全面的优化研究，包括pH，溶剂和温度。这些确定的温度为25°C，pH为7是保留对映选择性和活性的最佳条件。还确定了向有机转化混合物中添加有机溶剂的效果。研究结果表明，SET1仅适用于特定比例的所选有机水性介质。带有未保护和受保护的β-氨基腈（β的结构类似物）的分离物的官能团耐受性羟基腈的分离收率和选择性也很差，令人失望。分离物进一步用产生极佳收率和ee（> 99％（S）–异构体，收率50％）的α-氨基腈苯基甘氨腈生成酸进行评估。用该底物进行的一系列pH研究表明，pH 7是避免产物和底物降解的最佳p​​H。
• Analytical and preparative chiral supercritical fluid chromatography resolutions using crown ether‐derived column
  作者：Lei Yue、Larry Miller、John Reilly

  DOI：10.1002/chir.23621

  日期：2024.1

  addition of 5% water to the modifier dramatically improved the peak shape for chiral separation of primary amines on Crownpak® CR-I (+). The first reported preparative SFC separations on Crownpak® CR-I (+) are shown, offering a new approach for the preparative resolution of primary amines. The case studies demonstrate that Crownpak® CR-I (+) is a very useful column in the chiral separation of challenging compounds

  在本研究中，使用 12 种伯胺在 SFC 条件下对冠醚衍生色谱柱 Crownpak® CR-I (+) 进行了评估，并将色谱结果与八种固定化多糖色谱柱进行了比较。 Crownpak® CR-I (+) 取得了显着更高的成功率。结果发现，在改性剂中添加 5% 的水可显着改善 Crownpak® CR-I (+) 上伯胺手性分离的峰形。首次报道了在 Crownpak® CR-I (+) 上进行制备型 SFC 分离，为伯胺的制备型拆分提供了一种新方法。案例研究表明，Crownpak® CR-I (+) 是一种非常有用的色谱柱，可用于制药行业中含有伯胺基团的挑战性化合物的手性分离。
• Lopata, Antal; Faigl, Ferenc; Fogassy, Elemer, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2930 - 2952
  作者：Lopata, Antal、Faigl, Ferenc、Fogassy, Elemer、Darvas, Ferenc

  DOI：——

  日期：——
• A quantitative approach to optical resolution
  作者：Elemér Fogassy、Antal Lopata、Ferenc Faigl、Ferenc Darvas、Mária Ács、László Tõke

  DOI：10.1016/s0040-4039(01)85582-9

  日期：1980.1