4,4-dimethyl-2-[(2RS,3SR)-3-(4-nitrophenyl)-2-(2-nitrophenyl)oxiran-2-yl]-4,5-dihydro-1,3-oxazole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4-dimethyl-2-[(2RS,3SR)-3-(4-nitrophenyl)-2-(2-nitrophenyl)oxiran-2-yl]-4,5-dihydro-1,3-oxazole
• 英文别名: 4,4-dimethyl-2-[(2R,3S)-2-(2-nitrophenyl)-3-(4-nitrophenyl)oxiran-2-yl]-5H-1,3-oxazole
• 化学式: C₁₉H₁₇N₃O₆
• 分子量: 383.36
• InChiKey: OPMFNGOKRHKFPW-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,4-三甲基-2-恶唑 在 次氯酸叔丁酯 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 4,4-dimethyl-2-[(2RS,3SR)-3-(4-nitrophenyl)-2-(2-nitrophenyl)oxiran-2-yl]-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  One-Pot Regioselective Synthesis of Nitrophenyloxazolinyl Styrene Oxides by the Darzens Reaction of Vicarious Nucleophilic Substitution-Formed Carbanions of 2-Dichloromethyl-4,4-dimethyloxazoline

  摘要：

  The vicarious nucleophilic substitution reaction of dichloromethyloxazoline 2 with nitrobenzene has been investigated. Treatment of 2 with t-BuOK followed by the addition of nitrobenzene leads to benzylic carbanions 4 or 9 depending upon the solvent used (DMSO, DMF, or THF). Subsequent treatment of 4 or 9 with aldehydes, in a Darzens-like reaction, furnishes very good yields of nitrophenyl oxazolinyloxiranes 8 and 11. 1,2-Dioxazolinyl-1,2-dinitrophenylethene 7 forms quantitatively when carbanion 4 is allowed to warm to room temperature in the absence of external electrophiles.

  DOI：

  10.1021/jo0498359

文献信息

• One-Pot Regioselective Synthesis of Nitrophenyloxazolinyl Styrene Oxides by the Darzens Reaction of Vicarious Nucleophilic Substitution-Formed Carbanions of 2-Dichloromethyl-4,4-dimethyloxazoline
  作者：Saverio Florio、Patrizia Lorusso、Catia Granito、Renzo Luisi、Luigino Troisi

  DOI：10.1021/jo0498359

  日期：2004.7.1

  The vicarious nucleophilic substitution reaction of dichloromethyloxazoline 2 with nitrobenzene has been investigated. Treatment of 2 with t-BuOK followed by the addition of nitrobenzene leads to benzylic carbanions 4 or 9 depending upon the solvent used (DMSO, DMF, or THF). Subsequent treatment of 4 or 9 with aldehydes, in a Darzens-like reaction, furnishes very good yields of nitrophenyl oxazolinyloxiranes 8 and 11. 1,2-Dioxazolinyl-1,2-dinitrophenylethene 7 forms quantitatively when carbanion 4 is allowed to warm to room temperature in the absence of external electrophiles.