(S)-2-hydroxybut-3-enenitrile | 151592-44-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-hydroxybut-3-enenitrile
• 英文别名: (2S)-2-hydroxybut-3-enenitrile
• CAS: 151592-44-8
• 化学式: C₄H₅NO
• 分子量: 83.0898
• InChiKey: WKFMHXZXCCJSJK-BYPYZUCNSA-N

物化性质

• 沸点：
  195.2±20.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 (S)-2-hydroxybut-3-enenitrile 以126 mg的产率得到1-脱氧-D-木酮糖
  参考文献：
  名称：

  1-DEOXY-D-XYLULOSE SYNTHESIZED FROM THE (S)-CYANOHYDRIN OF ACROLEIN

  摘要：

  The biocatalytic transformation of acrolein into (S)-2-hydroxybut-3-enenitrile using the (S)-hydroxynitrile lyase from Hevea brasiliensis followed by Grignard C-elongation, asymmetric epoxidation and nucleophilic ring-opening afforded 1-deoxy-D-xylulose (1) in 47% overall yield.

  DOI：

  10.1081/car-100108660
• 作为产物：
  描述：

  氢氰酸 、 丙烯醛 在 hydroxynitrile lyase from Hevea brasiliensis 作用下， 以 水 为溶剂， 反应 0.25h， 以92%的产率得到(S)-2-hydroxybut-3-enenitrile
  参考文献：
  名称：

  在双相溶剂体系中酶催化醛和酮衍生的（S）-氰醇的形成

  摘要：

  通过使用剧烈搅拌的两相系统水性缓冲液/有机溶剂，并使用巴西橡胶树的羟基腈裂解酶作为生物催化剂，对映体纯（S）-氰醇从脂肪族，不饱和，芳香族和杂芳香族醛以及甲基烷基和甲基苯基酮中获得通常对映体过量98–99％。

  DOI：

  10.1016/s0040-4020(98)00901-6

文献信息

• Asymmetric carboncarbon bond forming reactions catalyzed by chiral Schiff base—titanium alkoxide complexes
  作者：Masahiko Hayashi、Tetsuya Inoue、Yasunori Miyamoto、Nobuki Oguni

  DOI：10.1016/s0040-4020(01)89374-1

  日期：1994.4

  The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96% e.e.). A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated

  在由四异丙醇钛[Ti（O- i- Pr）4 ]和手性席夫碱原位制备的催化剂的帮助下，将三甲基甲硅烷基氰化物对映选择性加成到各种醛中，从而以高光学收率得到了相应的氰醇（最多到96％ee）。通过将席夫碱加入到钛醇盐介导的醛的甲硅烷基氰化中，可以显着提高速率。该催化剂体系还促进了双烯酮与醛的高度对映选择性反应，这导致形成光学活性的5-羟基-3-氧代酯。
• Synthesis of α,β-unsaturated (S)-cyanohydrins using the oxynitrilase from Hevea brasiliensis
  作者：Norbert Klempier、Ulrike Pichler、Herfried Griengl

  DOI：10.1016/0957-4166(95)00085-4

  日期：1995.4

  α,β-unsaturated (S)-cyanohydrins derived from 2-propenal, 2-butenal, (E) and (Z)-2-hexenal and 2-hexynal are obtained in high enantiomeric purity (80–95% e.e.) by using an oxynitrilase isolated from the leaves of Hevea brasiliensis.

  通过使用以下方法获得高对映体纯度（80-95％ee）的衍生自2-丙烯醛，2-丁醛，（E）和（Z）-2-己醛和2-己醛的α，β-不饱和（S）-氰醇。从巴西橡胶树的叶片中分离出的一种氧硝化酶。
• Enantioselective trimethylsilylcyanation of some aldehydes catalyzed by chiral Schiff base-titanium alkoxide complexes
  作者：Masahiko Hayashi、Yasunori Miyamoto、Tetsuya Inoue、Nobuki Oguni

  DOI：10.1021/jo00058a037

  日期：1993.3

  A variety of aldehydes (aromatic, heteroaromatic, alpha,beta-unsaturated, and nonconjugate aliphatic aldehydes) has been trimethylsilylcyanated in highly enantiomeric excess (ee) with a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases. A remarkable rate enhancement was brought about by the addition of the Schiff base into the titanium alkoxide mediated silylcyanation of aldehydes. The chemical structure of chiral Schiff base-titanium alkoxide complexes is discussed based on their C-13 NMR spectra, field desorption (FD) mass spectra, and molecular weights.
• Aliphatic (S)-cyanohydrins by enzyme catalyzed synthesis
  作者：Norbert Klempier、Herfried Griengl、Marianne Hayn

  DOI：10.1016/s0040-4039(00)74084-6

  日期：1993.7

  The enzyme catalyzed synthesis of aliphatic (S)-cyanohydrins has been accomplished for the first time by application of a hydroxynitrile lyase from leaves of Hevea brasiliensis. The optical purities of (S)-cyanohydrins are in a range between 60-97%.
• Difficult substrates in the R-hydroxynitrile lyase catalyzed hydrocyanation reaction: application of the mass transfer limitation principle in a two-phase system
  作者：Pieter J. Gerrits、Jan Marcus、Lemonia Birikaki、Arne van der Gen

  DOI：10.1016/s0957-4166(01)00183-5

  日期：2001.5

  The application of a number of new and/or difficult substrates in the catalyzed hydrocyanation reaction by R-hydroxy nitrile lyase from almonds is described. By using an aqueous-organic two-phase system and increasing the rate of the enzymatic reaction relative re, the mass transfer rate, the enantiomeric purity was improved. By fine tuning the reaction parameters (temperature, pH. and the amount of enzyme) the hydrocyanation reaction was optimized for all substrates. The general principles described here can also be applied to optimize the reaction conditions: for other substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.