(S)-2-hydroxy-2-methylheptanenitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-hydroxy-2-methylheptanenitrile
• 英文别名: (2S)-2-hydroxy-2-methylheptanenitrile
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: QAXOKMZVYDLXEW-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-羟基-2-甲基庚腈 生成 (S)-2-hydroxy-2-methylheptanenitrile
  参考文献：
  名称：

  Approach to(R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

  摘要：

  The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones ((RRC)-R-1-C-2=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H>Me much greater than Et for R-2. In the case of aromatic methyl ketones reactivity difference (C6H5 much greater than p-Me-C6H4 for R-1) is notable. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00110-9

文献信息

• A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins
  作者：Samik Nanda、Yasuo Kato、Yasuhisa Asano

  DOI：10.1016/j.tet.2005.08.105

  日期：2005.11

  A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC

  从日本杏（Prunus mume）的种子中分离出一种新的羟腈裂解酶（HNL ）。该酶与从其他李属物种中分离的HNL具有相似的特性，并且是含FAD的酶。它接受大量非天然底物（苯甲醛及其变体）以添加HCN，从而以优异的光学和化学收率生产相应的氰醇。针对该酶开发了一种新的基于HPLC的对映选择性测定技术，该技术可促进在缓冲溶液（pH = 4.5）中将KCN添加到苯甲醛中。
• Synthesis of Aliphatic and α-Halogenated Ketone Cyanohydrins with the Hydroxynitrile Lyase from <i>Manihot esculenta</i>
  作者：Johannes Diebler、Jan von Langermann、Annett Mell、Martin Hein、Peter Langer、Udo Kragl

  DOI：10.1002/cctc.201300965

  日期：2014.4

  The potential of the hydroxynitrile lyase from Manihot esculenta towards ketone substrates was investigated. It was observed that the length of the aliphatic chain is a key parameter for the conversion of aliphatic, non‐branched ketones. Smaller substrates are readily converted with high enantioselectivites, but the elongation of the chain length causes a significant loss in enzyme activity. For a

  研究了来自Manihot esculenta的羟腈裂解酶对酮底物的潜力。据观察，脂族链的长度是脂族非支链酮转化的关键参数。较小的底物容易被高对映体选择物转化，但是链长的延长导致酶活性的显着降低。对于许多卤代，在此尤其是氟化的苯乙酮衍生物，已经合成了具有良好至中等对映选择性的相应的氰醇。
• Method for Producing Chiral Alpha-Hydroxycarboxylic Crystalline Acids
  申请人：Griengl Herfried

  公开号：US20060099696A1

  公开（公告）日：2006-05-11

  The invention relates to a method for producing chiral α-hydroxycarboxylic crystalline acids consisting in transforming cyanhydrins (R) or (S) into α-hydroxycarboxylic acids (R) or (S), respectively by enzymatic hydrolysis in the presence of Rhodococcus erythropolis NCIMB 11540.

  本发明涉及一种生产手性α-羟基羧酸结晶的方法，包括在以下物质存在的情况下，通过酶水解作用将氰醇(R)或(S)分别转化为α-羟基羧酸(R)或(S) 红球菌 NCIMB 11540。
• Method for producing chiral alpha-hydroxycarboxylic acids by enzymatic hydrolysis of chiral cyanohydrins
  申请人：Griengl Herfried

  公开号：US20060199256A1

  公开（公告）日：2006-09-07

  The invention relates to a method for producing chiral α-hydroxycarboxylic crystalline acids consisting in transforming cyanhydrins (R) or (S) into α-hydroxycarboxylic acids (R) or (S), respectively by enzymatic hydrolysis in the presence of Rhodococcus erythropolis NCIMB 11540.

  本发明涉及一种生产手性α-羟基羧酸结晶的方法，包括在以下物质存在的情况下，通过酶水解作用将氰醇(R)或(S)分别转化为α-羟基羧酸(R)或(S) 红球菌 NCIMB 11540。
• Foerster, Siegfried; Roos, Juergen; Effenberger, Franz, Angewandte Chemie, 1996, vol. 108, # 4, p. 493 - 494
  作者：Foerster, Siegfried、Roos, Juergen、Effenberger, Franz、Wajant, Harald、Sprauer, Achim

  DOI：——

  日期：——