(5R)-3,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 175226-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: (5R)-3,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-3,5-diphenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 175226-70-7
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: JGDBTEJQJXTQBM-AWEZNQCLSA-N

物化性质

• 沸点：
  394.3±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-3,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one 在 三氟化硼乙醚 作用下， 以 乙二醇二甲醚 、 正戊烷 为溶剂， 以34%的产率得到(5R)-3,5-diphenylmorpholin-2-one
  参考文献：
  名称：

  Diastereoselective Reduction of α-Imino Esters with Tris(trimethylsilyl)aluminum

  摘要：

  Tris(trimethylsilyl)aluminum was found to be a good chemoselective reducing reagent for alpha-imino esters to give alpha-amino esters in good yields. Application to the reduction of 3,5-disubstituted 5,6-dihyro-2H-1,4-oxazine2-ones realized a stereoselective conversion into cis-3,5-disubstituted morpholine-2-ones.

  DOI：

  10.3987/com-06-s(k)23
• 作为产物：
  描述：

  (4R)-2-benzyl-4-phenyl-2-oxazoline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以94%的产率得到(5R)-3,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  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.

  DOI：

  10.1021/jo952144f

文献信息

• An Efficient Entry to Optically Active <i>anti</i>- and <i>syn</i>-β-Amino-α-trifluoromethyl Alcohols
  作者：Santos Fustero、Laia Albert、José Luis Aceña、Juan F. Sanz-Cervera、Amparo Asensio

  DOI：10.1021/ol702947n

  日期：2008.2.1

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.
• 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.
• Diastereoselective Reduction of α-Imino Esters with Tris(trimethylsilyl)aluminum
  作者：Makoto Shimizu、Yasuki Niwa、Takeshi Nagai、Iwao Hachiya

  DOI：10.3987/com-06-s(k)23

  日期：——

  Tris(trimethylsilyl)aluminum was found to be a good chemoselective reducing reagent for alpha-imino esters to give alpha-amino esters in good yields. Application to the reduction of 3,5-disubstituted 5,6-dihyro-2H-1,4-oxazine2-ones realized a stereoselective conversion into cis-3,5-disubstituted morpholine-2-ones.