1-benzyl-3,3-dimethoxy-2-methylazetidine | 547753-60-6

• 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: 1-benzyl-3,3-dimethoxy-2-methylazetidine
• 英文别名: 1-Benzyl-3,3-dimethoxy-2-methylazetidine
• CAS: 547753-60-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: XKBILVZILJOAQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3,3-dimethoxy-2-methylazetidine 在 盐酸 作用下， 反应 12.0h， 以85%的产率得到1-benzyl-2-methylazetidin-3-one
  参考文献：
  名称：

  Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols

  摘要：

  Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-dimethoxyketimines, the resulting 3,3-dimethoxyazetidines being hydrolyzed by acid. Imination of these 1,2-disubstituted azetidin-3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2,4- and 2,2-dialkylated compounds. Analytical samples of the major 2,4-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00241-2
• 作为产物：
  描述：

  3,3-二甲氧基-2-丁酮 在 sodium tetrahydroborate 、 N,N-Diisopropylethylamine p-toluenesulfonate salt 、 四氯化钛 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 5.0h， 生成 1-benzyl-3,3-dimethoxy-2-methylazetidine
  参考文献：
  名称：

  Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols

  摘要：

  Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-dimethoxyketimines, the resulting 3,3-dimethoxyazetidines being hydrolyzed by acid. Imination of these 1,2-disubstituted azetidin-3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2,4- and 2,2-dialkylated compounds. Analytical samples of the major 2,4-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00241-2

文献信息

• Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols
  作者：Antonio Salgado、Yves Dejaegher、Guido Verniest、Mark Boeykens、Christine Gauthier、Christelle Lopin、Kourosch Abbaspour Tehrani、Norbert De Kimpe

  DOI：10.1016/s0040-4020(03)00241-2

  日期：2003.3

  Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-dimethoxyketimines, the resulting 3,3-dimethoxyazetidines being hydrolyzed by acid. Imination of these 1,2-disubstituted azetidin-3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2,4- and 2,2-dialkylated compounds. Analytical samples of the major 2,4-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved.