| 1092696-24-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• CAS: 1092696-24-6
• 化学式: C₆H₁₀Cl₄O₂
• 分子量: 255.956
• InChiKey: QNAFACNEEIFHIK-ZXXMMSQZSA-N

反应信息

• 作为反应物：
  描述：

  、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(2R,3S,4S,5R)-6-(acetyloxy)-2,3,4,5-tetrachlorohexyl acetate
  参考文献：
  名称：

  Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited

  摘要：

  Polychlorinated hydrocarbon motifs have been synthesized in enantiomerically pure forms by means of nucleophilic multiple chlorinations of chiral epoxides, which stereospecifically incorporate halogen atoms into oxygenated molecular scaffolds. The present study demonstrates the scope of the N-chlorosuccinimide (NCS)/organophosphine reagent system that forms multiple sp(3)C-Cl bonds in a regularly repeating pattern, with proper stereochemical configurations and evaluates its applicability to various epoxides having elaborate structures. It is noteworthy that tetrachlorinated motifs are produced in one step from bisepoxides by using NCS/Ph3P. Furthermore, Ph2PCl used in combination with NCS has been found to serve as a potentially useful alternative to NCS/Ph3P, especially for promoting dichlorination reactions of alkenyl-substituted epoxides.

  DOI：

  10.1021/jo802093d
• 作为产物：
  描述：

  在 10% Pd(OH)2/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以6 mg的产率得到
  参考文献：
  名称：

  Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited

  摘要：

  Polychlorinated hydrocarbon motifs have been synthesized in enantiomerically pure forms by means of nucleophilic multiple chlorinations of chiral epoxides, which stereospecifically incorporate halogen atoms into oxygenated molecular scaffolds. The present study demonstrates the scope of the N-chlorosuccinimide (NCS)/organophosphine reagent system that forms multiple sp(3)C-Cl bonds in a regularly repeating pattern, with proper stereochemical configurations and evaluates its applicability to various epoxides having elaborate structures. It is noteworthy that tetrachlorinated motifs are produced in one step from bisepoxides by using NCS/Ph3P. Furthermore, Ph2PCl used in combination with NCS has been found to serve as a potentially useful alternative to NCS/Ph3P, especially for promoting dichlorination reactions of alkenyl-substituted epoxides.

  DOI：

  10.1021/jo802093d