trans-1-benzyl-2-ethyl-2-methyl-4-(phenylselanylmethyl)azetidine

• 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: trans-1-benzyl-2-ethyl-2-methyl-4-(phenylselanylmethyl)azetidine
• 英文别名: (2R,4S)-1-benzyl-2-ethyl-2-methyl-4-(phenylselanylmethyl)azetidine
• 化学式: C₂₀H₂₅NSe
• 分子量: 358.385
• InChiKey: LNGFYYKUCHDSMZ-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-butanone N-benzylimine 在 sodium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 16.0h， 生成 trans-1-benzyl-2-ethyl-2-methyl-4-(phenylselanylmethyl)azetidine
  参考文献：
  名称：

  Synthesis of Azetidine and Pyrrolidine Derivatives through Selenium-Induced Cyclization of Secondary Homoallylamines − A77Se NMR Study

  摘要：

  Treatment of alpha-alkyl and alpha,alpha-dialkyl homoallylic amines I with PhSeX (X = Cl, Br, 1), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by Se-77 NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77 Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the alpha-carbon, but also with the nature of the counterion X- (PhSeCl < PhSeBr < PhSeI). Use of PhSeI and amines 1g to 1k (R-1, R-2, not equalH), produced only the azetidinium. salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by Se-77 NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromose-lenuranes 8 were detected. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200203)2002:6<995::aid-ejoc995>3.0.co;2-a

文献信息

• Synthesis of Azetidine and Pyrrolidine Derivatives through Selenium-Induced Cyclization of Secondary Homoallylamines − A77Se NMR Study
  作者：Xavier Pannecoucke、Francis Outurquin、Claude Paulmier

  DOI：10.1002/1099-0690(200203)2002:6<995::aid-ejoc995>3.0.co;2-a

  日期：2002.3

  Treatment of alpha-alkyl and alpha,alpha-dialkyl homoallylic amines I with PhSeX (X = Cl, Br, 1), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by Se-77 NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77 Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the alpha-carbon, but also with the nature of the counterion X- (PhSeCl < PhSeBr < PhSeI). Use of PhSeI and amines 1g to 1k (R-1, R-2, not equalH), produced only the azetidinium. salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by Se-77 NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromose-lenuranes 8 were detected. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.