(2S)-2,3-dibromopropan-1-ol | 83165-36-0

• 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: (2S)-2,3-dibromopropan-1-ol
• 英文别名: (S)-2,3-dibromo-1-propanol
• CAS: 83165-36-0
• 化学式: C₃H₆Br₂O
• 分子量: 217.888
• InChiKey: QWVCIORZLNBIIC-GSVOUGTGSA-N

物化性质

• 沸点：
  203.3±0.0 °C(Predicted)
• 密度：
  2.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-2,3-dibromopropan-1-ol 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.75h， 以85%的产率得到(R)-2-(溴甲基)环氧乙烷
  参考文献：
  名称：

  Crystallization-Induced Asymmetric Transformations. Enantiomerically pure (−)-(R)- and (+)-(S)-2,3-Dibromopropan-1-ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters

  摘要：

  (S)-2,3-Dibromopropan-1-ol of high enantiomer excess was obtained by crystallization-induced asymmetric transformations of racemic 2,3-dibromopropan-1-ol esterified with N-([1,1'-biphenyl]-4-ylcarbonyl-L-alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.

  DOI：

  10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a
• 作为产物：
  描述：

  2,3-二溴-1-丙醇 生成 (2S)-2,3-dibromopropan-1-ol
  参考文献：
  名称：

  TAKANO, SEHJITI;OGASAVARA, KUNIRO;SEHKIGUTI, IOSIKOTO;KITAMURA, TORU;KASA+

  摘要：

  DOI：

文献信息

• Haloalkane dehalogenase catalysed desymmetrisation and tandem kinetic resolution for the preparation of chiral haloalcohols
  作者：Alja Westerbeek、Jan G.E. van Leeuwen、Wiktor Szymański、Ben L. Feringa、Dick B. Janssen

  DOI：10.1016/j.tet.2012.06.059

  日期：2012.9

  Six different bacterial haloalkane dehalogenases were recombinantly produced in Escherichia coli, purified, and used to catalyse the conversion of prochiral short-chain dihaloalkanes and a meso dihaloalkane, yielding enantioenriched haloalcohols. A two-reaction one-enzyme process was established in which the desymmetrisation of a dihaloalkane is followed by kinetic resolution of the chiral haloalcohol that is produced in the first step. In case of 1,3-dibromo-2-methylpropane and 1,3-dibromo-2-phenylpropane, an increase of the enantiomeric excess of the respective haloalcohol was observed in time, leading to ee values of >97%, with analytical yields of 24 and 52%, respectively. The results show that haloalkane dehalogenases can be used for the production of highly enantioenriched haloalcohols and that in some cases product enantiopurity can be improved by allowing a two-step one-enzyme tandem reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Diastereoselective bromination of allyl glycosides using tetrabutylammonium tribromide
  作者：Giuseppe Bellucci、Cinzia Chiappe、Felicia D'Andrea

  DOI：10.1016/0957-4166(94)00378-o

  日期：1995.1

  Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60% have been obtained by diastereoselective addition of Bq to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or Cd using tetrabutylammonium tribromide, followed by hydrolysis. The absolute configuration is shown to depend on the position of the free hydroxyl and on the configuration at the anomeric centre.
• TAKANO, SEHJITI;OGASAVARA, KUNIRO;SEHKIGUTI, IOSIKOTO;KITAMURA, TORU;KASA+
  作者：TAKANO, SEHJITI、OGASAVARA, KUNIRO、SEHKIGUTI, IOSIKOTO、KITAMURA, TORU、KASA+

  DOI：——

  日期：——
• Crystallization-Induced Asymmetric Transformations. Enantiomerically pure (−)-(R)- and (+)-(S)-2,3-Dibromopropan-1-ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters
  作者：Gabriella Brunetto、Susanna Gori、Rita Fiaschi、Elio Napolitano

  DOI：10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a

  日期：2002.11

  (S)-2,3-Dibromopropan-1-ol of high enantiomer excess was obtained by crystallization-induced asymmetric transformations of racemic 2,3-dibromopropan-1-ol esterified with N-([1,1'-biphenyl]-4-ylcarbonyl-L-alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.