(4R,5R)-3,4-dimethyl-5-phenyloxazolidin-2-imine

• 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: (4R,5R)-3,4-dimethyl-5-phenyloxazolidin-2-imine
• 英文别名: (4R,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-imine
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: AINPTMZQNYUGDW-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  盐酸右旋麻黄碱 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 22.25h， 生成 (4R,5R)-3,4-dimethyl-5-phenyloxazolidin-2-imine
  参考文献：
  名称：

  Reactivity of chlorodeoxypseudoephedrines with oxo-, thio-, and selenocyanates

  摘要：

  Herein, the reactivity of chlorodeoxypseudoephedrine hydrochlorides with oxo-, thio-, and selenocyanate nucleophiles is reported. 1,3-Heterazolidine-2-iminium or ammonium salts were obtained stereo selectively in most cases. The hard-soft nature of the calcogen atom determines the mechanistic pathway via an S(N)2 (X = O), aziridine intermediate (X = Se), or both (X = S). A simple method to synthesize stereoselectively the trans-isomer of 3,4-dimethyl-5-phenyl-oxazolidine-2-iminium chloride and the cis-isomer of 4-methyl-5-phenyl-oxazoline-2-ammonium chloride, was also found. In addition, heterazolidine-2-imines or amines were liberated from the corresponding salts [Cl- or XCN- (X = O, S, Se)] with aqueous NaOH. Finally, cis-3,4-dimethyl-5-phenyl-oxazolidine-2-iminium chloride, cis-4-methyl-5-phenyl-oxazoline-2-amine, and trans-4-methyl-5-phenyl-selenazoline-2-amine compounds were studied by X-ray diffraction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.012

文献信息

• Synthesis of optically active boroxazolidine, borathiazolidine and boraselenazolidine and their N-borane adducts from the corresponding 2-imino-heteroazolidines
  作者：Alejandro Cruz、Diana Macías-Mendoza、Efraín Barragan-Rodríguez、Hugo Tlahuext、Heinrich Nöth、Rosalinda Contreras

  DOI：10.1016/s0957-4166(97)00591-0

  日期：1997.12

  The synthesis from the corresponding 2-imino-heteroazolidines of optically active boroxazolidine, borathiazolidine and boraselenazolidine, derived from ephedrine, and their N-borane adducts is reported. The X-ray diffraction structures of (4R,5R)-(+)-3,4-dimethyl-5-phenyl-2-iminium thiazolidine thiocyanate 9b, (4R,5R)-(+)-3,4-dimethyl-5-phenyl-2-iminium-selenazolidine selenocyanate 9c, (4R,5R)-(+)-3,4-dimethyl-5-phenyl-2-iminoselenazolidine 10b and (4R,5R)-(+)-3,4-dimethyl-5-phenyl-2-boraselenazolidine dimer 15 were elucidated. Compounds were also studied by H-1, C-13 and Se-77 NMR. (C) 1997 Elsevier Science Ltd. All rights reserved.