(S)-5-bromo-1-cyanopentyl alcohol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-5-bromo-1-cyanopentyl alcohol
• 英文别名: (2S)-6-bromo-2-hydroxyhexanenitrile
• 化学式: C₆H₁₀BrNO
• 分子量: 192.055
• InChiKey: HUEBAVYAKKLUDU-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  5-bromo-1-cyanopentyl acetate 在 Candida antarctica lipase B 、 水 作用下， 以 甲苯 为溶剂， 生成 (R)-5-bromo-1-cyanopentyl acetate 、 (S)-5-bromo-1-cyanopentyl alcohol
  参考文献：
  名称：

  Enantioenriched ω-bromocyanohydrin derivatives. Improved selectivity by combination of two chiral catalysts

  摘要：

  Highly enantioenriched (R)-4-bromo-1-cyanobutyl acetate and (R)-5-bromo-1-cyanopentyl acetate were prepared by acetylcyanation of 4-bromobutanal and 5-bromopentanal, respectively, catalyzed by (S,S)-[(4,6-bis(t-butyl)salen)Ti(mu-O)](2) and triethylamine followed by enzymatic hydrolysis of the minor enantiomer. A cyclic procedure employing the same two chiral catalysts provided inferior results due to a slowly reached steady state and, in reactions with the former substrate, to ring-closure of the free cyanohydrin formed as an intermediate in the reaction. Hydrolysis of the acylated cyanohydrins followed by AgClO4-promoted cyclization provided (R)-2-cyanotetrahydrofuran and (R)-2-cyanotetrahydropyran in essentially enantiopure form. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.090

文献信息

• Chemoenzymatic synthesis of (S)-2-cyanopiperidine, a key intermediate in the route to (S)-pipecolic acid and 2-substituted piperidine alkaloids
  作者：Serge Nazabadioko、Ramón J Pérez、Rosario Brieva、Vicente Gotor

  DOI：10.1016/s0957-4166(98)00140-2

  日期：1998.5

  preparation of (S)-2-cyanopiperidine 4 provides a new access to 2-substituted piperidines. This synthesis is based on an enantioselective (R)-oxynitrilase-catalyzed reaction for the preparation of (R)-(+)-6-bromo-2-hydroxyhexanenitrile 1 and the subsequent cyclization of this compound to yield the piperidine ring. The utilization of 4 as the starting material for the synthesis of (S)-2-aminomethylpiperidine

  （S）-2-氰基哌啶4的制备为2-取代的哌啶提供了新的途径。该合成基于对映选择性（R）-氧硝腈酶催化的反应，该反应用于制备（R）-（+）-6-溴-2-羟基己腈1，随后将该化合物环化以产生哌啶环。还描述了使用4作为起始原料来合成（S）-2-氨基甲基哌啶6，（R）-（-）-亚氨酸10和（S）-（-）-哌酸13。
• Optically active (S)-ketone- and (R)-aldehyde-cyanohydrins via an (R)-oxynitrifase-catalysed transcyanation. Chemoenzymatic syntheses of 2-cyanotetrahydrofuran and 2-cyanotetrahydropyran
  作者：Emma Menéndez、Rosario Brieva、Francisca Rebolledo、Vicente Gotor

  DOI：10.1039/c39950000989

  日期：——

  (R)-Oxynitrilase catalyses the enantioselective decyanation of racemic ketone cyanohydrins and the enantioselective addition of HCN to ω-bromoaldehydes in one step.

  (R)-氧炔基三里酶可催化外消旋酮类氰醇的对映体选择性脱氰反应，以及一步完成 HCN 与 ω-bromoaldehydes 的对映体选择性加成反应。
• Application of crude preparations of leaves from food plants for the formation of cyanohydrins with high enantiomeric excesses
  作者：Liliana Hernández、Héctor Luna、Aída Solís、Alfredo Vázquez

  DOI：10.1016/j.tetasy.2006.10.015

  日期：2006.10

  Crude preparations obtained from mamey (Pouteria sapota), capulin (Prunus serotina var. capulli) and peach (Prunus persica) leaves were used to catalyze the enantioselective addition of HCN to a variety of aldehydes. The corresponding cyanohydrins were obtained with high levels of enantioselectivity, comparable with those obtained with other catalysts used for the same purpose. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioenriched ω-bromocyanohydrin derivatives. Improved selectivity by combination of two chiral catalysts
  作者：Robin Hertzberg、Khalid Widyan、Berenice Heid、Christina Moberg

  DOI：10.1016/j.tet.2012.05.090

  日期：2012.9

  Highly enantioenriched (R)-4-bromo-1-cyanobutyl acetate and (R)-5-bromo-1-cyanopentyl acetate were prepared by acetylcyanation of 4-bromobutanal and 5-bromopentanal, respectively, catalyzed by (S,S)-[(4,6-bis(t-butyl)salen)Ti(mu-O)](2) and triethylamine followed by enzymatic hydrolysis of the minor enantiomer. A cyclic procedure employing the same two chiral catalysts provided inferior results due to a slowly reached steady state and, in reactions with the former substrate, to ring-closure of the free cyanohydrin formed as an intermediate in the reaction. Hydrolysis of the acylated cyanohydrins followed by AgClO4-promoted cyclization provided (R)-2-cyanotetrahydrofuran and (R)-2-cyanotetrahydropyran in essentially enantiopure form. (C) 2012 Elsevier Ltd. All rights reserved.