3-bromo-2-butanol

• 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-bromo-2-butanol
• 英文别名: threo-3-Brombutan-2-ol；(2R,3R)-(+)-3-bromo-2-butanol；(2RS,3RS)-3-bromo-butan-2-ol；(2R*,3R*)-3-Bromo-2-butanol；(2R,3R)-3-bromobutan-2-ol
• 化学式: C₄H₉BrO
• 分子量: 153.019
• InChiKey: JCYSVJNMXBWPHS-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  1
• 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：

  3-bromo-2-butanol 、 水 生成 丁酮
  参考文献：
  名称：

  ANGELINI, G.;SPERANZA, M., J. AMER. CHEM. SOC., 1981, 103, N 13, 3800-3806

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二甲基环氧乙烷 在 Ipc₂BBr 作用下， 以 正戊烷 为溶剂， 反应 0.5h， 以69%的产率得到3-bromo-2-butanol
  参考文献：
  名称：

  内消旋环氧化物与 B-卤代二异松蒎基硼烷的对映选择性环裂解

  摘要：

  摘要：B-卤代二异松蒎基硼烷，IpcBX，特别是溴化物 1b 和碘化物 1c，可区分内消旋环氧化物的对映体碳氧键，以提供中等至优异对映体纯度的 1,2-卤代醇。因此 (-)-(1R, 2R)-2-溴环己醇，(-)-(1R, 2R)-2-碘代环己醇，(-)-(1R, 2R)-2-碘代环己-4-en-1-o1和 (-)-(1R, 2R)-2-bromocyclohex-4-en-1-o1 分别以 84%、91%、63% 和 95% ee 从相应的内消旋环氧化物和卤代硼烷试剂中获得。然后从戊烷中简单重结晶得到基本上 100% ee 的卤代醇；顺式-2-氧化丁烯和顺式-3-氧化己烯分别以78% 和69% ee 提供相应的(1R, 2R)-碘醇。在所有情况下，内消旋环氧化物的 S 碳都被选择性裂解。这是对内消旋环氧化物进行对映选择性开环以获得光学活性 1,2-卤代醇的第一个例子。关键词：不对称合成。

  DOI：

  10.1021/ja00226a050

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.
• Asymmetric ring opening of meso-epoxides with B-halobis(2-isocaranyl)boranes 2-dIcr2BX
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1016/j.tetasy.2006.06.044

  日期：2006.8

  Hydroboration of commercially available (+)-2-carene (96% ee) with either BH2Cl center dot SMe2 or BC13/Me3SiH, provides chemically pure B-chlorobis(2-isocaranyl)borane (2-(d)Icr(2)BCl) whereas B-bromobis(2-isocaranyl)borane (2-(d)Icr(2)BBr) could only be prepared by Matteson's BBr3/Me3SiH procedure in high chemical yield and purity. The enantionteric excess achieved with 2-(d)Icr(2)BCl (78%), was significantly higher than those realized with the previously explored reagent, (IPC2BCl)-I-d (41%), especially for meso-cyclohexene oxide. The new reagent, 2-(d) Icr(2)BBr also showed considerable improvements in enantiomeric excesses, in the cases of meso-cyclopentene oxide (67%) and meso-cis-2,3-butene oxide (78%) than those achieved with the previously reported reagent, (IPC2BBr)-I-d (57% and 61%, respectively). (c) 2006 Elsevier Ltd. All rights reserved.
• Srebnik, M.; Joshi, N. N.; Brown, Herbert C., Israel Journal of Chemistry, 1989, vol. 29, p. 229 - 238
  作者：Srebnik, M.、Joshi, N. N.、Brown, Herbert C.

  DOI：——

  日期：——
• Preparation of the four stereoisomers of 3-bromo-2-butanol or their acetates via lipase-catalysed resolutions of the racemates derived from dl- or meso-2,3-butanediol
  作者：Rong Liu、Per Berglund、Hans-Erik Högberg

  DOI：10.1016/j.tetasy.2005.06.028

  日期：2005.8

  The four stereoisomeric 3-bromo-2-butanols and/or their acetates were prepared via lipase-catalysed kinetic resolution by hydrolyses of the acetates of the (+/-)-syn- and (+/-)-anti-3-bromo-2-butanols, or via esterifications of the alc hols. The diastereomeric bromoacetates were obtained by syntheses from the dl- and meso-2,3-butanediols, respectively. On a preparative scale, the four stereoisomers, either as the free alcohols or as their acetates, were obtained in > 95% ee, and in 35-40% yield (based on the starting racemates). (c) 2005 Elsevier Ltd. All rights reserved.
• MAGUET M.; POIRIER Y.; GUGLIELMETTI R., BULL. SOC. CHIM. FRANCE, 1978, PART 2, NO 11-12, 550-560
  作者：MAGUET M.、 POIRIER Y.、 GUGLIELMETTI R.

  DOI：——

  日期：——