(R)-(+)-5-溴-2-羟基戊腈 | 164472-76-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(+)-5-溴-2-羟基戊腈
• 英文名称: (R)-(+)-5-bromo-2-hydroxypentanenitrile
• 英文别名: (R)-4-bromo-1-cyanobutyl alcohol；(2R)-5-bromo-2-hydroxypentanenitrile
• CAS: 164472-76-8
• 化学式: C₅H₈BrNO
• 分子量: 178.029
• InChiKey: CAESAWJWFMMWJE-RXMQYKEDSA-N

物化性质

• 沸点：
  312.8±32.0 °C(Predicted)
• 密度：
  1.541±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-溴-2-羟基戊腈 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (R)-哌啶-3-醇
  参考文献：
  名称：

  Chemoenzymatic synthesis of azacycloalkan-3-ols

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00351-1
• 作为产物：
  描述：

  (R)-4-bromo-1-cyanobutyl acetate 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 44.5h， 以93%的产率得到(R)-(+)-5-溴-2-羟基戊腈
  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。
• Stereocontrolled chemoenzymatic synthesis of 2,3-disubstituted piperidines
  作者：Maria I. Monterde、Rosario Brieva、Vicente Gotor

  DOI：10.1016/s0957-4166(01)00080-5

  日期：2001.3

  (R,R)-2,3-Disubstituted piperidines were readily synthesized starting from (R)-(+)- 5-bromo-2-hydroxypentanenitrile (R)-2. An enantioselective (R)-oxynitrilase-catalyzed transcyanation was used to prepare the starting cyanohydrin (R)-2. (C) 2001 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 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.