(4R)-2-benzyl-4-phenyl-2-oxazoline | 73713-21-0

• 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)-2-benzyl-4-phenyl-2-oxazoline
• 英文别名: (4R)-2-Benzyl-4-phenyl-4,5-dihydro-1,3-oxazole；(4R)-2-benzyl-4-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 73713-21-0
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: SARRDFOUWJAWBU-HNNXBMFYSA-N

物化性质

• 沸点：
  376.7±41.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-2-benzyl-4-phenyl-2-oxazoline 在 氧气 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric addition of organometallics to chiral ketooxazolines. Preparation of enantiomerically enriched .alpha.-hydroxy acids

  摘要：

  DOI：

  10.1021/jo01302a008
• 作为产物：
  描述：

  N-phenylacetyl-(R)-phenylglycinol 在 copper(II) bis(trifluoromethanesulfonate) 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以79%的产率得到(4R)-2-benzyl-4-phenyl-2-oxazoline
  参考文献：
  名称：

  Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide

  摘要：

  N-(beta-Hydroxy)amides can be cyclised by reaction with diisopropy1carbodiimide (DIC) to give the corresponding 2-oxazolines in high yields. The reaction requires only very mild Lewis-acid catalysis (5mol% Cu(OTf)(2)) and can be accomplished with simple heating, or in very short reaction times under microwave irradiation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.143

文献信息

• Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2<i>H</i>-1,4-oxazin-2-ones and Morpholin-2-ones
  作者：Cynthia M. Shafer、Tadeusz F. Molinski

  DOI：10.1021/jo952144f

  日期：1996.1.1

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.
• Asymmetric addition of organometallics to chiral ketooxazolines. Preparation of enantiomerically enriched .alpha.-hydroxy acids
  作者：A. I. Meyers、Joel Slade

  DOI：10.1021/jo01302a008

  日期：1980.7
• Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide
  作者：Stefano Crosignani、Abigail C. Young、Bruno Linclau

  DOI：10.1016/j.tetlet.2004.10.143

  日期：2004.12

  N-(beta-Hydroxy)amides can be cyclised by reaction with diisopropy1carbodiimide (DIC) to give the corresponding 2-oxazolines in high yields. The reaction requires only very mild Lewis-acid catalysis (5mol% Cu(OTf)(2)) and can be accomplished with simple heating, or in very short reaction times under microwave irradiation. (C) 2004 Elsevier Ltd. All rights reserved.