2-(bromomethyl)-1-s-butyl-4,4-dimethylpyrrolidine | 279250-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(bromomethyl)-1-s-butyl-4,4-dimethylpyrrolidine
• 英文别名: 2-(Bromomethyl)-1-butan-2-yl-4,4-dimethylpyrrolidine；2-(bromomethyl)-1-butan-2-yl-4,4-dimethylpyrrolidine
• CAS: 279250-63-4
• 化学式: C₁₁H₂₂BrN
• 分子量: 248.206
• InChiKey: JZCYTOWJCISZFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-1-s-butyl-4,4-dimethylpyrrolidine 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以81%的产率得到1-Butan-2-yl-5,5-dimethylpiperidin-3-one
  参考文献：
  名称：

  Reduction of 5-(bromomethyl)-1-pyrrolinium bromides to 2-(bromomethyl)pyrrolidines and their transformation into piperidin-3-ones through an unprecedented ring expansion-oxidation protocol

  摘要：

  3,3-Dialkyl-5-(bromomethyl)-1-pyrrolinium bromides, prepared via bromocyclization of N-(2,2-dialkyl-4-pentenylidene)amines by means of bromine in dichloromethane, were reduced to 4,4-dialkyl-2-(bromomethyl)pyrrolidines for the first time using borane dimethyl sulfide in dichloromethane. Furthermore, the latter 2-(bromomethyl)pyrrolidines were transformed into the corresponding piperidin-3-ones through an unprecedented ring expansion-oxidation protocol in dimethylsulfoxide in the presence potassium carbonate. Reduction of 5,5-dialkylpiperidin-3-ones by means of sodium borohydride in methanol afforded 5,5-dialkyl-3-hydroxypiperidines in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.112
• 作为产物：
  描述：

  1-Butan-2-yl-2,5-dimethoxy-3,3-dimethylpiperidine 在 sodium tetrahydroborate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-(bromomethyl)-1-s-butyl-4,4-dimethylpyrrolidine
  参考文献：
  名称：

  Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to 2-(bromomethyl)pyrrolidines

  摘要：

  3-Methoxypiperidines were converted into 2-(bromomethyl)pyrrolidines by reaction with boron(III) bromide in dichloromethane. This reaction proceeds via an intermediate bicyclic aziridinium ion and features a rare conversion of piperidines into pyrrolidines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00191-x

文献信息

• Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to 2-(bromomethyl)pyrrolidines
  作者：Kourosch Abbaspour Tehrani、Kris Van Syngel、Mark Boelens、Jan Contreras、Norbert De Kimpe、David W Knight

  DOI：10.1016/s0040-4039(00)00191-x

  日期：2000.4

  3-Methoxypiperidines were converted into 2-(bromomethyl)pyrrolidines by reaction with boron(III) bromide in dichloromethane. This reaction proceeds via an intermediate bicyclic aziridinium ion and features a rare conversion of piperidines into pyrrolidines. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Reduction of 5-(bromomethyl)-1-pyrrolinium bromides to 2-(bromomethyl)pyrrolidines and their transformation into piperidin-3-ones through an unprecedented ring expansion-oxidation protocol
  作者：Matthias D’hooghe、Jan Baele、Jan Contreras、Mark Boelens、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2008.07.112

  日期：2008.10

  3,3-Dialkyl-5-(bromomethyl)-1-pyrrolinium bromides, prepared via bromocyclization of N-(2,2-dialkyl-4-pentenylidene)amines by means of bromine in dichloromethane, were reduced to 4,4-dialkyl-2-(bromomethyl)pyrrolidines for the first time using borane dimethyl sulfide in dichloromethane. Furthermore, the latter 2-(bromomethyl)pyrrolidines were transformed into the corresponding piperidin-3-ones through an unprecedented ring expansion-oxidation protocol in dimethylsulfoxide in the presence potassium carbonate. Reduction of 5,5-dialkylpiperidin-3-ones by means of sodium borohydride in methanol afforded 5,5-dialkyl-3-hydroxypiperidines in good yields. (C) 2008 Elsevier Ltd. All rights reserved.