trans-3-(1-hydroxy-2-trityloxyethyl)-2-phenyl-1-methylazetidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: trans-3-(1-hydroxy-2-trityloxyethyl)-2-phenyl-1-methylazetidine
• 英文别名: 1-[(2R,3R)-1-methyl-2-phenylazetidin-3-yl]-2-trityloxyethanol
• 化学式: C₃₁H₃₁NO₂
• 分子量: 449.593
• InChiKey: QHFOQEPYSSVCEU-ZLZIOLORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	trans-1-methyl-2-phenyl-3-[1-(trimethylsilyloxy)-2-(trityloxy)ethyl]azetidine	——	C34H39NO2Si	521.775

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 trans-3-(1-hydroxy-2-trityloxyethyl)-2-phenyl-1-methylazetidine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以93%的产率得到trans-1-methyl-2-phenyl-3-[1-(trimethylsilyloxy)-2-(trityloxy)ethyl]azetidine
  参考文献：
  名称：

  Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

  摘要：

  A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.014
• 作为产物：
  描述：

  cis-N-Benzyl-N-methyl-2-aminomethyl-3-(trityloxymethyl)oxirane 在 正丁基锂 、 potassium tert-butylate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以75%的产率得到trans-3-(1-hydroxy-2-trityloxyethyl)-2-phenyl-1-methylazetidine
  参考文献：
  名称：

  Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

  摘要：

  A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.014

文献信息

• Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines
  作者：Ferenc Faigl、Ervin Kovács、Gábor Turczel、Áron Szöllősy、Alessandro Mordini、László Balázs、Tamás Holczbauer、Mátyás Czugler

  DOI：10.1016/j.tetasy.2012.10.014

  日期：2012.12

  A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.