(P,2'S,4'S,5'R)-N,N-diethyl-2-(3,4-dimehyl-5-phenyl-1,3-oxazolan-2-yl)-6-ethylbenzamide

• 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: (P,2'S,4'S,5'R)-N,N-diethyl-2-(3,4-dimehyl-5-phenyl-1,3-oxazolan-2-yl)-6-ethylbenzamide
• 英文别名: 2-[(2S,4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl]-N,N,6-triethylbenzamide
• 化学式: C₂₄H₃₂N₂O₂
• 分子量: 380.53
• InChiKey: ATMGSONOROSOCF-OWSXEPHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-diethyl-2-formyl-6-(1-trimethylsilylethyl)benzamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 (P,2'S,4'S,5'R)-N,N-diethyl-2-(3,4-dimehyl-5-phenyl-1,3-oxazolan-2-yl)-6-ethylbenzamide
  参考文献：
  名称：

  使用脯氨酸衍生的咪唑啉和麻黄碱衍生的恶唑烷类化合物动态拆分阻转异构酰胺

  摘要：

  阻转异构的叔2-甲酰基萘酰胺或2-甲酰基苯甲酰胺与一些手性二胺和氨基醇的缩合通过动态拆分过程导致带有手性咪唑烷或恶唑烷的叔酰胺的单一阻转异构体。新杂环的水解与起始醛的动态热力学拆分竞争，并且快速还原可分离出对映异构体富集形式的带有2-羟甲基取代基的阻转异构酰胺。提供了反应在热力学控制下的证据。

  DOI：

  10.1016/j.tet.2004.01.101

文献信息

• Using amide conformation to ‘project’ the stereochemistry of an (−)-ephedrine-derived oxazolidine: a pair of pseudoenantiomeric chiral amido-phosphine ligands
  作者：Jonathan Clayden、Lai Wah Lai、Madeleine Helliwell

  DOI：10.1016/s0957-4166(01)00110-0

  日期：2001.4

  Protection of a tertiary 2-formylbenzamide as an (-)-ephedrine-derived oxazolidine both Fords the amide's stereogenic Ar-CO axis to adopt one of two possible diastereoisomeric conformations and protects the formyl group from attack during amide ortho-lithiation. By functionalising the amide in the 6-position, reactive sites (such as -CHO, -SR, -PR2 groups) may be introduced which fall under the stereochemical influence, relayed by the amide: of the (-)-ephedrine-derived oxazolidine. This 'projection' of stereochemistry is exemplified by a pair of amido-phosphines. members of the first ever class of non-biaryl atropisomeric ligands, which are made functionally pseudoenantiomeric by the intervention of either one or two amide groups between the (-)-ephedrine-derived oxazolidine and the PPh2 group. The pseudoenantiomeric amido-phosphines promote the palladium-catalysed asymmetric allylation of dimethyl malonate in 82 and -53% e.e., respectively. (C) 2001 Published by Elsevier Science Ltd.
• Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines
  作者：Jonathan Clayden、Lai Wah Lai、Madeleine Helliwell

  DOI：10.1016/j.tet.2004.01.101

  日期：2004.5

  some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched

  阻转异构的叔2-甲酰基萘酰胺或2-甲酰基苯甲酰胺与一些手性二胺和氨基醇的缩合通过动态拆分过程导致带有手性咪唑烷或恶唑烷的叔酰胺的单一阻转异构体。新杂环的水解与起始醛的动态热力学拆分竞争，并且快速还原可分离出对映异构体富集形式的带有2-羟甲基取代基的阻转异构酰胺。提供了反应在热力学控制下的证据。