1-异丙基-5,5-二甲基-3-哌啶酮 | 177703-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-异丙基-5,5-二甲基-3-哌啶酮
• 中文别名: 3-哌啶酮,5,5-二甲基-1-(1-甲基乙基)-(9CI)
• 英文名称: 1-Isopropyl-5,5-dimethyl-piperidin-3-one
• 英文别名: 5,5-Dimethyl-1-propan-2-ylpiperidin-3-one
• CAS: 177703-67-2
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: KGVQPYZYXOFQSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-异丙基-5,5-二甲基-3-哌啶酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以73%的产率得到5,5-Dimethyl-1-propan-2-ylpiperidin-3-ol
  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：

  在 盐酸 、 溴 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-异丙基-5,5-二甲基-3-哌啶酮
  参考文献：
  名称：

  Rearrangement of 5-(bromomethyl)-1-pyrrolinium salts into functionalized piperidines

  摘要：

  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

  DOI：

  10.1016/0040-4039(96)00487-x

文献信息

• 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.
• 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