1-Tert-butyl-3,3-diethyl-5-methoxypiperidine | 177703-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Tert-butyl-3,3-diethyl-5-methoxypiperidine
• CAS: 177703-64-9
• 化学式: C₁₄H₂₉NO
• 分子量: 227.39
• InChiKey: RUUAXCJAKBMSQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Tert-butyl-3,3-diethyl-5-methoxypiperidine 在 三溴化硼 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以84%的产率得到2-(Bromomethyl)-1-tert-butyl-4,4-diethylpyrrolidine
  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
• 作为产物：
  描述：

  1-Tert-butyl-3,3-diethyl-2,5-dimethoxypiperidine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 1-Tert-butyl-3,3-diethyl-5-methoxypiperidine
  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

• Rearrangement of 5-(bromomethyl)-1-pyrrolinium salts into functionalized piperidines
  作者：Norbert De Kimpe、Mark Boelens、Jan Contreras

  DOI：10.1016/0040-4039(96)00487-x

  日期：1996.4

  5-(Bromomethyl)-1-pyrrolinium bromides undergo rearrangement with alkoxides in the corresponding alcohol to afford 2,5-dialkoxypiperidines, which are easily converted into 3-alkoxypiperidines. 2,5-Dialkoxypiperidines undergo a peculiar thermal rearrangement to afford 5-alkoxy-1,2,3,4-tetrahydropyridines. Copyright (C) 1996 Elsevier Science Ltd
• 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.