3-Hydroxy-4-fluor-butyronitril | 1537-89-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 3-Hydroxy-4-fluor-butyronitril
• 英文别名: 4-Fluoro-3-hydroxybutanenitrile
• CAS: 1537-89-9
• 化学式: C₄H₆FNO
• 分子量: 103.096
• InChiKey: SSLJCTIHTDMEDU-UHFFFAOYSA-N

物化性质

• 沸点：
  83-84 °C(Press: 1 Torr)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-4-fluor-butyronitril 在 吡啶 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 γ-Fluor-β-phosphonooxy-butyronitril
  参考文献：
  名称：

  提取酯XXXII的形成和转化。pH值的新单质氰基醇酰基磷酸酯和不同pH值的断裂

  摘要：

  描述了一些新的氰基烷基磷酸单酯的合成及其断裂速率。在β-氰基烷基-磷酸单酯的情况下，当在β位置上的两个H被烷基取代时，在碱性介质中单酯基团不再被去磷酸化。

  DOI：

  10.1002/hlca.19620450340
• 作为产物：
  描述：

  环氧氟丙烷 、 sodium cyanide 在 cell-free extract containing HheB₂ in TMEG buffer 作用下， 以 aq. acetate buffer 为溶剂， 反应 3.0h， 以84%的产率得到3-Hydroxy-4-fluor-butyronitril
  参考文献：
  名称：

  Halohydrin dehalogenase-catalysed transformations of epifluorohydrin

  摘要：

  Biocatalytic ring-opening of epifluorohydrin has been performed by using halohydrin dehalogenase. The enzyme from Mycobacterium sp. GP1 (HheB2) catalysed reaction with high regioselectivity and low enantioselectivity in the presence of different nucleophiles, producing racemic 1-substituted 3-fluoro-2-propanols. No by-products resulting from the ring-closure reaction have been detected, confirming that vicinal fluoro alcohols are not substrates for HHDH. Four different 3-fiuoro-2-propanols were prepared under mild reaction conditions starting from epifluorohydrin. High conversions of 85-100% were reached within 1-3 h and depending on the nucleophile used products were isolated in 31-92% yields. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.12.054

文献信息

• Recherches sur la formation et la transformation de dérivés organiques du fluor III. Préparation d'hydroxy-acides, d'hydroxy-nitriles, d'hydroxy-esters et d'hydroxy-éthers fluorés ainsi que de leurs dérivé phosphorylés
  作者：Emile Cherbuliez、A. de Picciotto、J. Rabinowitz

  DOI：10.1002/hlca.19600430426

  日期：——

  Some new fluorinated hydroxy-acids and hydroxy-ethers as well as their phosphorylated derivatives are described.

  描述了一些新的氟化羟基酸和羟基醚以及它们的磷酸化衍生物。
• Biosynthesis of Salinosporamides from α,β-Unsaturated Fatty Acids: Implications for Extending Polyketide Synthase Diversity
  作者：Yuan Liu、Christopher Hazzard、Alessandra S. Eustáquio、Kevin A. Reynolds、Bradley S. Moore

  DOI：10.1021/ja9042824

  日期：2009.8.5

  A new series of coenzyme A-tethered polyketide synthase extender units were discovered in relation to the biosynthesis of the salinosporamide family of anticancer agents from the marine bacterium Salinispora tropica. In vivo and in vitro experiments revealed that the crotonyl-CoA reductase/carboxylase SalG has broad substrate tolerance toward 2-alkenyl-CoAs that give rise to the salinosporamide C-2 substitution pattern.
• 669. Organic fluorine compounds. Part XX. Some reactions of 1-chloro-3-fluoropropan-2-ol and epifluorohydrin
  作者：Ernst D. Bergmann、Sasson Cohen、Israel Shahak

  DOI：10.1039/jr9610003448

  日期：——
• Recherches sur la formation et la transformation des esters XXXII. Sur la préparation de quelques nouveaux monoesters cyanoalcoyl-phosphoriques et sur leur vitesse de scission à différents pH
  作者：Emile Cherbuliez、H. Probst、J. Rabinowitz

  DOI：10.1002/hlca.19620450340

  日期：——

  The synthesis and the rate of scission of some new cyanoalkyl-phosphoric monoesters are described. In the case of β-cyanoalkyl-phosphoric monoesters, the monoester group is no more dephosphorylated in alkaline medium when the two H in the β position are substituted by alkyl groups.

  描述了一些新的氰基烷基磷酸单酯的合成及其断裂速率。在β-氰基烷基-磷酸单酯的情况下，当在β位置上的两个H被烷基取代时，在碱性介质中单酯基团不再被去磷酸化。
• Halohydrin dehalogenase-catalysed transformations of epifluorohydrin
  作者：Maja Majerić Elenkov、Mirjana Čičak、Ana Smolko、Anamarija Knežević

  DOI：10.1016/j.tetlet.2017.12.054

  日期：2018.1

  Biocatalytic ring-opening of epifluorohydrin has been performed by using halohydrin dehalogenase. The enzyme from Mycobacterium sp. GP1 (HheB2) catalysed reaction with high regioselectivity and low enantioselectivity in the presence of different nucleophiles, producing racemic 1-substituted 3-fluoro-2-propanols. No by-products resulting from the ring-closure reaction have been detected, confirming that vicinal fluoro alcohols are not substrates for HHDH. Four different 3-fiuoro-2-propanols were prepared under mild reaction conditions starting from epifluorohydrin. High conversions of 85-100% were reached within 1-3 h and depending on the nucleophile used products were isolated in 31-92% yields. (C) 2017 Elsevier Ltd. All rights reserved.