(2S,3R)-3,5-diphenylmorpholinone | 173167-55-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-3,5-diphenylmorpholinone
• 英文别名: (3S,5R)-3,5-diphenylmorpholin-2-one
• CAS: 173167-55-0
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: BDFBIWDQLNJRBG-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3,5-diphenylmorpholinone 在 正硅酸甲酯 、 硼烷 、 cesium fluoride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.5h， 生成 (4R,8S,8aR)-8-methyl-4,8a-diphenyl-4,6,7,8-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazin-1-one
  参考文献：
  名称：

  Enantiomerically Pure 3-Substituted 2-Phenylprolines by Caesium Fluoride/Tetramethoxysilane Mediated 1,4-Addition of 3(S)-5(R)-Diphenylmorpholin-2-one to Acrylates

  摘要：

  DOI：

  10.1055/s-1997-947
• 作为产物：
  描述：

  (4R)-2-benzyl-4-phenyl-2-oxazoline 在 palladium on activated charcoal selenium(IV) oxide 、 氢气 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (2S,3R)-3,5-diphenylmorpholinone
  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

• α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids
  作者：T.K. Chakraborty、K. Azhar Hussain、G. Venkat Reddy

  DOI：10.1016/0040-4020(95)00523-b

  日期：1995.8

  The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative cleavage make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular

  使用廉价的α-苯基甘氨醇作为手性助剂，在Strecker合成中实现了很高的非对映选择性，并且通过氧化裂解可轻松去除，这使其成为大规模制备旋光性α-氨基酸（尤其是糖肽类抗生素中大量存在的α-芳基甘氨酸）的理想选择。按照这种方法可以合成许多手性氨基酸。还进行了分子力学计算以解释观察到的非对映选择。
• Synthesis of α-phenyl proline derivatives via 1,3-dipolar cycloaddition of chiral stabilised azomethine ylids
  作者：Amberley.S. Anslow、Laurence.M. Harwood、Ian.A. Lilley

  DOI：10.1016/0957-4166(95)00321-f

  日期：1995.10

  The preparation of (3S, 5R)-3,5-diphenylmorpholinone 1 and subsequent diastereoselective 1,3-dipolar cycloaddition of its formaldehyde derived azomethine ylid is described. Removal of the chiral template furnishes α-phenyl proline derivatives.

  描述了（3 S，5 R）-3,5-二苯基吗啉酮1的制备及其甲醛衍生的偶氮甲亚胺基化合物的随后的非对映选择性1,3-偶极环加成反应。手性模板的去除提供了α-苯基脯氨酸衍生物。
• 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.
• Enantiomerically Pure 3-Substituted 2-Phenylprolines by Caesium Fluoride/Tetramethoxysilane Mediated 1,4-Addition of 3(<i>S</i>)-5(<i>R</i>)-Diphenylmorpholin-2-one to Acrylates
  作者：Laurence Harwood、Giles Hamblett、Antonio Jiménez-Díaz、David Watkin

  DOI：10.1055/s-1997-947

  日期：1997.8