(R)-5-bromo-1-cyanopentyl alcohol | 164472-77-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-5-bromo-1-cyanopentyl alcohol
• 英文别名: (2R)-6-bromo-2-hydroxyhexanenitrile
• CAS: 164472-77-9
• 化学式: C₆H₁₀BrNO
• 分子量: 192.055
• InChiKey: HUEBAVYAKKLUDU-ZCFIWIBFSA-N

物化性质

• 沸点：
  308.1±32.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (R)-5-bromo-1-cyanopentyl alcohol 在 palladium dihydroxide 吡啶 、 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 145.25h， 生成 L-哌啶-2-甲酸
  参考文献：
  名称：

  化学酶促合成（S）-2-氰基哌啶，这是通向（S）-哌酸和2-取代哌啶生物碱的关键中间体

  摘要：

  （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。

  DOI：

  10.1016/s0957-4166(98)00140-2
• 作为产物：
  描述：

  5-溴戊醛 在 di-μ-oxo-di((S,S)-N,N'-bis((salicylaldehydo)ethylenediamine))dititanium(IV) 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.5h， 生成 (R)-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

• 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。
• Chemoenzymatic synthesis of azacycloalkan-3-ols
  作者：Maria I Monterde、Serge Nazabadioko、Francisca Rebolledo、Rosario Brieva、Vicente Gotor

  DOI：10.1016/s0957-4166(99)00351-1

  日期：1999.8

  Optically active omega-bromocyanohydrins are easily synthesized through an enantioselective (R)-oxynitrilase-catalyzed reaction from their corresponding omega-bromoaldehydes. These cyanohydrins are starting materials for the preparation of medium size nitro gen heterocycles. The reduction of (R)-(+)-5-bromo-2-hydroxypentanenitrile affords, in one-pot, piperidin-3-ol. Azepan-3-ol and azocan-3-ol are readily obtained from their corresponding cyanohydrins in high enantiomeric excesses. (C) 1999 Elsevier Science 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.
• 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。