4-((N-benzylmethylamino)methyl)-5-((trityloxy)methyl)oxazolidin-2-one

• 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-((N-benzylmethylamino)methyl)-5-((trityloxy)methyl)oxazolidin-2-one
• 英文别名: (4R,5S)-4-[[benzyl(methyl)amino]methyl]-5-(trityloxymethyl)-1,3-oxazolidin-2-one
• 化学式: C₃₂H₃₂N₂O₃
• 分子量: 492.618
• InChiKey: NALQHBWKIWTLNW-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S,5R)-4-trityloxymethyl-3-oxa-1-azabicyclo[3.1.0]hexan-2-one 、 N-甲基苄胺 以 二氯甲烷 为溶剂， 以54%的产率得到4-((N-benzylmethylamino)methyl)-5-((trityloxy)methyl)oxazolidin-2-one
  参考文献：
  名称：

  Studies on the ring opening reactions of 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones. Synthesis of aminomethyl oxazolidinones and aziridinyl ureas

  摘要：

  The reaction of fused ring aziridines, 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones, with amine nucleophiles can provide either an aminomethyl oxazolidinone or an aziridinyl urea. The amine, reaction solvent, and aziridine substitution have been examined with the aid of computational studies to identify reaction conditions that provide a single product. Polar solvents provided only the aminomethyl oxazolidinone products. Formation of aziridinyl ureas required control of aziridine substitution, solvent, and reactant stoichiometry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.071

文献信息

• Studies on the ring opening reactions of 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones. Synthesis of aminomethyl oxazolidinones and aziridinyl ureas
  作者：Greggory M. Wells、Travis Dudding、Lee Belding、Jeffery A. Frick、Abhijit Nayek、Junfeng Huang、Steven J. Katz、Stephen C. Bergmeier

  DOI：10.1016/j.tet.2012.03.071

  日期：2012.5

  The reaction of fused ring aziridines, 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones, with amine nucleophiles can provide either an aminomethyl oxazolidinone or an aziridinyl urea. The amine, reaction solvent, and aziridine substitution have been examined with the aid of computational studies to identify reaction conditions that provide a single product. Polar solvents provided only the aminomethyl oxazolidinone products. Formation of aziridinyl ureas required control of aziridine substitution, solvent, and reactant stoichiometry. (C) 2012 Elsevier Ltd. All rights reserved.