(2RS,3SR)-2,3-dibromohexane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (2RS,3SR)-2,3-dibromohexane
• 英文别名: threo-2,3-dibromohexane；2,3-dibromohexane；erythro-2,3-dibromohexane；Hexane, 2,3-dibromo-, erythro；(2S,3R)-2,3-dibromohexane
• 化学式: C₆H₁₂Br₂
• 分子量: 243.969
• InChiKey: CHNCACSQVNDLSU-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  反-2-已烯 在 Br₃^(1-)*C₁₉H₁₇PPol⁽¹⁺⁾ 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(2RS,3SR)-2,3-dibromohexane
  参考文献：
  名称：

  带有三溴甲基三苯基phosph基团的珠子的顺序溴化反应

  摘要：

  已经开发了一种基于聚苯乙烯珠的可重复使用的溴化试剂，该聚苯乙烯珠具有共价连接的三溴化甲基三苯基phosph基团。描述了几种结构上不同的不饱和底物与微珠和非聚合型溴化剂三溴甲基三苯基phosph溶液的溴化反应的结果。结果表明，该反应具有很高的区域选择性和立体选择性，并且易于进行。版权所有©2010 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1694

文献信息

• A mild and efficient sonochemical bromination of alkenes using tetrabutylammonium tribromide
  作者：Jacques Berthelot、Yamina Benammar、Catherine Lange

  DOI：10.1016/s0040-4039(00)79884-4

  日期：1991.8

  The bromination of substituted alkenes using tetrabutylammonium tribromide can be effectued under mild conditions with ultrasonic irradiation. This process gives quantitatively the corresponding vicinal dibromide in high yield.

  使用三溴化四丁基铵的取代烯烃的溴化反应可以在温和的条件下通过超声波辐照进行。该过程以高产率定量给出相应的邻位二溴化物。
• Sequential bromination reactions from beads with methyltriphenylphosphonium tribromide groups
  作者：Rodrigo Cristiano、Andrew D. Walls、Richard G. Weiss

  DOI：10.1002/poc.1694

  日期：——

  A reusable bromination reagent based on polystyrene beads with covalently appended methyltriphenylphosphonium tribromide groups has been developed. The results from bromination reactions of several structurally diverse unsaturated substrates with the beads and with solutions of a non‐polymeric model brominating reagent, methyltriphenylphosphonium tribromide, are described. It is shown that the reactions

  已经开发了一种基于聚苯乙烯珠的可重复使用的溴化试剂，该聚苯乙烯珠具有共价连接的三溴化甲基三苯基phosph基团。描述了几种结构上不同的不饱和底物与微珠和非聚合型溴化剂三溴甲基三苯基phosph溶液的溴化反应的结果。结果表明，该反应具有很高的区域选择性和立体选择性，并且易于进行。版权所有©2010 John Wiley＆Sons，Ltd.
• High Quantum Yield Molecular Bromine Photoelimination from Mononuclear Platinum(IV) Complexes
  作者：Alice Raphael Karikachery、Han Baek Lee、Mehdi Masjedi、Andreas Ross、Morgan A. Moody、Xiaochen Cai、Megan Chui、Carl D. Hoff、Paul R. Sharp

  DOI：10.1021/ic4004998

  日期：2013.4.1

  Pt(IV) complexes trans-Pt(PEt3)(2)(R)(Br)(3) (R = Br, aryl and polycyclic aromatic fragments) photoeliminate molecular bromine with quantum yields as high as 82%. Photoelimination occurs both in the solid state and in solution. Calorimetry measurements and DFT calculations (PMe3 analogs) indicate endothermic and endergonic photoeliminations with free energies from 2 to 22 kcal/mol of Br-2. Solution trapping experiments with high concentrations of 2,3-dimethyl-2-butene suggest a radical-like excited state precursor to bromine elimination.
• Teets, Thomas S.; Nocera, Daniel G., Journal of the American Chemical Society, 2009, vol. 131, p. 7411 - 7420
  作者：Teets, Thomas S.、Nocera, Daniel G.

  DOI：——

  日期：——
• Stereoselective Bromination Reactions Using Tridecylmethylphosphonium Tribromide in a “Stacked” Reactor
  作者：Kefeng Ma、Shaw Li、Richard G. Weiss

  DOI：10.1021/ol801327n

  日期：2008.10.2

  A new reagent, tridecylmethylphosphonium tribromide, and new procedures for bromination reactions of unsaturated substrates (including one that allows several substrates to be reacted in sequence) are described. The procedures exploit the diffusion of components and the densities and immiscibilities of layers, including a fluorous "spacer" layer, within a reaction vessel. The stereoselectivities achieved in-the reactions are superior in some cases to those found with other brominating reagents.