3-Benzyl-8-methyl-1-propyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione | 429685-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Benzyl-8-methyl-1-propyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione
• 英文别名: 3-Benzyl-8-methyl-1-propyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione；3-benzyl-8-methyl-1-propyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione
• CAS: 429685-66-5
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: KDELOVXADRONFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Benzyl-8-methyl-1-propyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-Benzyl-8-methyl-1-propyl-3,8-diaza-bicyclo[3.2.1]octane
  参考文献：
  名称：

  Tandem cyclisation and [2,3]-Stevens rearrangement to 2-substituted pyrrolidines

  摘要：

  Reaction of N-methylallylamine with diethyl meso-2,5-dibromoadipate in DMF at ambient temperature in the presence of potassium carbonate led directly to the two diastereomers of diethyl 2-allyl-N-methylpyrroliditie-2.5-dicarboxylate. The reaction proceeds via a [2,3]-sigmatropic Stevens rearrangement, which occurred spontaneously under the reaction conditions. This gave a higher yield under milder conditions than the traditional Stevens reaction of diethyl N-allylpyrrolidine-2,5-dicarboxylate with iodomethane. The sequence was a key step in the synthesis of a series of analogues of the alkaloid stemofoline. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02286-9
• 作为产物：
  描述：

  diethyl meso-2,5-dibromoadipate 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 230.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 3-Benzyl-8-methyl-1-propyl-3,8-diaza-bicyclo[3.2.1]octane-2,4-dione
  参考文献：
  名称：

  Tandem cyclisation and [2,3]-Stevens rearrangement to 2-substituted pyrrolidines

  摘要：

  Reaction of N-methylallylamine with diethyl meso-2,5-dibromoadipate in DMF at ambient temperature in the presence of potassium carbonate led directly to the two diastereomers of diethyl 2-allyl-N-methylpyrroliditie-2.5-dicarboxylate. The reaction proceeds via a [2,3]-sigmatropic Stevens rearrangement, which occurred spontaneously under the reaction conditions. This gave a higher yield under milder conditions than the traditional Stevens reaction of diethyl N-allylpyrrolidine-2,5-dicarboxylate with iodomethane. The sequence was a key step in the synthesis of a series of analogues of the alkaloid stemofoline. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02286-9

文献信息

• Tandem cyclisation and [2,3]-Stevens rearrangement to 2-substituted pyrrolidines
  作者：Stephen C Smith、Philip D Bentley

  DOI：10.1016/s0040-4039(01)02286-9

  日期：2002.1

  Reaction of N-methylallylamine with diethyl meso-2,5-dibromoadipate in DMF at ambient temperature in the presence of potassium carbonate led directly to the two diastereomers of diethyl 2-allyl-N-methylpyrroliditie-2.5-dicarboxylate. The reaction proceeds via a [2,3]-sigmatropic Stevens rearrangement, which occurred spontaneously under the reaction conditions. This gave a higher yield under milder conditions than the traditional Stevens reaction of diethyl N-allylpyrrolidine-2,5-dicarboxylate with iodomethane. The sequence was a key step in the synthesis of a series of analogues of the alkaloid stemofoline. (C) 2002 Elsevier Science Ltd. All rights reserved.