苏-3-溴-2-丁醇 | 5798-80-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: 苏-3-溴-2-丁醇
• 英文名称: threo-3-bromo-2-butanol
• 英文别名: 3-bromobutan-2-ol；(2RS,3RS)-3-bromo-butan-2-ol；(+/-)-threo-3-bromo-butan-2-ol；(+/-)-threo-3-Brom-butan-2-ol；(+/-)-threo-3-Brom-butanol-(2)；dl-threo-3-Hydroxy-2-brom-butan；(2S,3S)-3-Bromo-2-butanol；(2S,3S)-3-bromobutan-2-ol
• CAS: 5798-80-1；19246-39-0；19246-40-3；19773-40-1；19773-41-2；49623-62-3；116051-24-2；122673-95-4；127304-30-7
• 化学式: C₄H₉BrO
• 分子量: 153.019
• InChiKey: JCYSVJNMXBWPHS-IMJSIDKUSA-N

物化性质

• 沸点：
  154°C (rough estimate)
• 密度：
  1.4550

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：

  苏-3-溴-2-丁醇 在 (R, R)-(salen)Co(II) 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 120.0h， 生成 2,3-cis-epoxybutane
  参考文献：
  名称：

  Catalytic Asymmetric Cyclization of Some Bromohydrins with Chiral Cobalt Complex

  摘要：

  在存在光学活性的钴(salen)型复杂物的情况下，研究了多种溴醇与碱的非对称环化反应。获得了光学纯度适中的光学活性环氧烷。赤霉-3-溴-2-丁醇和反霉-3-溴-2-丁醇进行了类似的环化，分别仅获得了反-2,3-二甲基环氧烷和顺-2,3-二甲基环氧烷，这表明溴醇的环化过程通过完全的SN2型反应进行。

  DOI：

  10.1246/bcsj.61.603
• 作为产物：
  描述：

  顺-2-丁烯 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 溶剂黄146 为溶剂， 生成 苏-3-溴-2-丁醇
  参考文献：
  名称：

  Desulfurization of episulfides, a sulfurane reaction

  摘要：

  DOI：

  10.1021/jo00945a020

文献信息

• Monobromoborane - Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1071/ch06408

  日期：——

  Monobromoborane–dimethyl sulfide (BH2Br–SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at –25°C, 4-chlorobenzaldehyde still underwent 12–13% reduction of an aldehydic group.

  单溴硼烷二甲基硫醚（BH2Br-SMe2）是一种具有高度区域性和化学选择性的试剂，除了是一种出色的氢硼酸化试剂外，还可在 0°C 温度下，在烯、炔、醚、乙缩醛、酮和丙酮的存在下，将环氧分子溴化裂解成溴水酐。在这种转化过程中，可以容纳多种活性官能团，如氯化物、酮、酯、腈、亚硝基和硫醚。虽然苯乙酮的还原反应在零下 25 摄氏度时被完全抑制，但 4-氯苯甲醛仍能还原 12-13% 的醛基。
• Radical cyclization of O-trityl oximino esters: a ring closure that preserves the oxime function
  作者：Derrick L. J. Clive、Rajendra Subedi

  DOI：10.1039/a908842c

  日期：——

  O-Trityl oximino esters 1 undergo stannane-induced radical cyclization to regenerate an oxime function, affording oximino lactones 4; these can be converted into enamides (e.g. 11b), and such a transformation was used to make the natural product 14c.

  O 型三苯甲基肟酯 1 在锡烷的诱导下发生自由基环化反应，重新生成肟功能，从而得到肟内酯 4；这些内酯可转化为酰胺（如 11b），这种转化被用于制造天然产物 14c。
• Bafford,R.A. et al., Bulletin de la Societe Chimique de France, 1973, p. 971 - 977
  作者：Bafford,R.A. et al.

  DOI：——

  日期：——
• 212. Dithiols. Part XXI. Dithiols from cyclic trithiocarbonates
  作者：S. M. Iqbal、L. N. Owen

  DOI：10.1039/jr9600001030

  日期：——
• 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.