tert-butyl-[(Z)-2-chloro-4-phenylmethoxybut-2-enoxy]-dimethylsilane | 1092695-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl-[(Z)-2-chloro-4-phenylmethoxybut-2-enoxy]-dimethylsilane
• CAS: 1092695-68-5
• 化学式: C₁₇H₂₇ClO₂Si
• 分子量: 326.939
• InChiKey: SISZNJXTSGNZLT-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S,3R)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以69%的产率得到[(2R,3S)-4-(benzyloxy)-2,3-dichlorobutoxy](tert-butyl)dimethylsilane
  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

文献信息

• Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited
  作者：Takehiko Yoshimitsu、Naoya Fukumoto、Tetsuaki Tanaka

  DOI：10.1021/jo802093d

  日期：2009.1.16

  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.