4,4-dimethyl-2-((2RS,3SR)-3-phenylthio-1-tritylaziridin-2-yl)-4,5-dihydrooxazole

• 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: 4,4-dimethyl-2-((2RS,3SR)-3-phenylthio-1-tritylaziridin-2-yl)-4,5-dihydrooxazole
• 英文别名: 4,4-dimethyl-2-[(2R,3S)-3-phenylsulfanyl-1-tritylaziridin-2-yl]-5H-1,3-oxazole
• 化学式: C₃₂H₃₀N₂OS
• 分子量: 490.669
• InChiKey: MXADWNBLLMCFCP-KLWTVMBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-三苯甲基-2-氮丙啶羧酸甲酯 在 lanthanum(III) chloride 、 正丁基锂 、 四甲基乙二胺 、 二乙胺基三氟化硫 、 仲丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 4,4-dimethyl-2-((2RS,3SR)-3-phenylthio-1-tritylaziridin-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Regio- and Stereoselective Lithiation of Terminal Oxazolinylaziridines:  The Aziridine N-Substituent and the Oxazolinyl Group Effect

  摘要：

  The regioselective lithiation of terminal oxazolinylaziridines has been investigated. The steric hindrance of the nitrogen substituent in 1-trityl-2-oxazolinylaziridine 3a, combined with the coordinating ability of the oxazolinyl group, causes beta-lithiation, whereas a completely regioselective alpha-lithiation is observed with the much less sterically demanding 1-benzyl-2-oxazolinylaziridine 3c and a competition between alpha- and beta-lithiation occurs with 1-cumyl-2-oxazolinylaziridine 3b in which the N-substituent has a steric hindrance in between the trityl and the benzyl groups. The application of the lithiation-trapping sequence for the preparation of enantioenriched 2,3-cis-disubstituted oxazolinylaziridines and aziridino-gamma-lactones is also reported.

  DOI：

  10.1021/ol071264u

文献信息

• Regio- and Stereoselective Lithiation of Terminal Oxazolinylaziridines:  The Aziridine <i>N</i>-Substituent and the Oxazolinyl Group Effect
  作者：Renzo Luisi、Vito Capriati、Peppino Di Cunto、Saverio Florio、Rosmara Mansueto

  DOI：10.1021/ol071264u

  日期：2007.8.1

  The regioselective lithiation of terminal oxazolinylaziridines has been investigated. The steric hindrance of the nitrogen substituent in 1-trityl-2-oxazolinylaziridine 3a, combined with the coordinating ability of the oxazolinyl group, causes beta-lithiation, whereas a completely regioselective alpha-lithiation is observed with the much less sterically demanding 1-benzyl-2-oxazolinylaziridine 3c and a competition between alpha- and beta-lithiation occurs with 1-cumyl-2-oxazolinylaziridine 3b in which the N-substituent has a steric hindrance in between the trityl and the benzyl groups. The application of the lithiation-trapping sequence for the preparation of enantioenriched 2,3-cis-disubstituted oxazolinylaziridines and aziridino-gamma-lactones is also reported.