1-(4-methylbenzyl)azetidine-3-carbonitrile | 1353650-41-5

• 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-(4-methylbenzyl)azetidine-3-carbonitrile
• 英文别名: 3-methyl-1-(4-methylbenzyl)azetidine-3-carbonitrile；3-Methyl-1-(4-methylbenzyl)azetidine-3-carbonitrile；3-methyl-1-[(4-methylphenyl)methyl]azetidine-3-carbonitrile
• CAS: 1353650-41-5
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: CXJRVRGADMFQFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methylbenzyl)azetidine-3-carbonitrile 在 ammonium hydroxide 、 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 ammonium 3-methyl-1-(4-methylbenzyl)azetidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of 3-functionalized 3-methylazetidines

  摘要：

  1-t-Butyl- and 1-(4-methylbenzyl)-3-bromo-3-methylazetidines were prepared from the corresponding N-(2,3-dibromo-2-methylpropylidene)alkylamines and their propensity to undergo nucleophilic substitution at the 3-position by different nucleophiles was assessed, providing a convenient access to novel 3-alkoxy-, 3-aryloxy-, 3-hydroxy-, 3-cyano-, 3-carboxy-, 3-(aminomethyl)- and 3-(hydroxymethyl)azetidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.097
• 作为产物：
  描述：

  2,3-dibromo-2-methyl-N-[(4-methylphenyl)methyl]propan-1-imine 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 61.0h， 生成 1-(4-methylbenzyl)azetidine-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 3-functionalized 3-methylazetidines

  摘要：

  1-t-Butyl- and 1-(4-methylbenzyl)-3-bromo-3-methylazetidines were prepared from the corresponding N-(2,3-dibromo-2-methylpropylidene)alkylamines and their propensity to undergo nucleophilic substitution at the 3-position by different nucleophiles was assessed, providing a convenient access to novel 3-alkoxy-, 3-aryloxy-, 3-hydroxy-, 3-cyano-, 3-carboxy-, 3-(aminomethyl)- and 3-(hydroxymethyl)azetidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.097

文献信息

• Solvent-Controlled Selective Transformation of 2-Bromomethyl-2-methylaziridines to Functionalized Aziridines and Azetidines
  作者：Sonja Stanković、Hannelore Goossens、Saron Catak、Meniz Tezcan、Michel Waroquier、Veronique Van Speybroeck、Matthias D’hooghe、Norbert De Kimpe

  DOI：10.1021/jo202637a

  日期：2012.4.6

  The reactivity of 2-bromomethyl-2-methylaziridines toward oxygen, sulfur, and carbon nucleophiles in different solvent systems was investigated. Remarkably, the choice of the solvent has a profound influence on the reaction outcome, enabling the selective formation of either functionalized aziridines in dimethylformamide (through direct bromide displacement) or azetidines in acetonitrile (through rearrangement

  研究了2-溴甲基-2-甲基氮丙啶在不同溶剂体系中对氧，硫和碳亲核试剂的反应性。值得注意的是，溶剂的选择对反应结果有深远的影响，能够选择性地形成二甲基甲酰胺中的官能化氮丙啶（通过直接溴化物置换）或乙腈中的氮杂环丁烷（通过双环叠氮基中间体重排）。另外，通过DFT计算进一步支持了实验观察到的2-溴甲基-2-甲基氮丙啶的溶剂依赖性行为。
• Synthesis of 3-functionalized 3-methylazetidines
  作者：Sonja Stanković、Matthias D’hooghe、Kourosch Abbaspour Tehrani、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2011.10.097

  日期：2012.1

  1-t-Butyl- and 1-(4-methylbenzyl)-3-bromo-3-methylazetidines were prepared from the corresponding N-(2,3-dibromo-2-methylpropylidene)alkylamines and their propensity to undergo nucleophilic substitution at the 3-position by different nucleophiles was assessed, providing a convenient access to novel 3-alkoxy-, 3-aryloxy-, 3-hydroxy-, 3-cyano-, 3-carboxy-, 3-(aminomethyl)- and 3-(hydroxymethyl)azetidines. (C) 2011 Elsevier Ltd. All rights reserved.