(S)-N1-(2,6-diisopropylphenyl)-N2-(2-hydroxy-1-phenylethyl)oxalamide | 1414649-05-0

• 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: (S)-N1-(2,6-diisopropylphenyl)-N2-(2-hydroxy-1-phenylethyl)oxalamide
• CAS: 1414649-05-0
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: FGYAUBDKVTWUHB-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.43
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N1-(2,6-diisopropylphenyl)-N2-(2-hydroxy-1-phenylethyl)oxalamide 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-(4-(1-(benzyloxy)-3-phenylpropan-2-yl)-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-ylidene)gold(I) chloride
  参考文献：
  名称：

  Asymmetric induction afforded by chiral azolylidene N-heterocyclic carbenes (NHC) catalysts

  摘要：

  Screening studies of new chiral imidazolium and triazolium based NHC salts I-VIII as ligands in asymmetric organometallic catalysis and as organocatalysts showed that these catalysts efficiently promoted the reactions. Moderate enantioselectivities (55-57% ee) were obtained in the asymmetric Cu-NHC catalysed conjugate additions of diethylzinc to cyclohexenone, in accordance with most previous studies. The chiral induction afforded in the gold(I)-NHC catalysed cyclopropanation reactions was low (< 28% ee). However, these results represent the first reported chiral gold(I)-NHC catalysed olefin cyclopropanation. The NHC-organocatalysed asymmetric cross-annulation of cinnamaldehyde and trifluoroacetophenone gave lower enantioselectivity (< 50% ee) but higher yields of the gamma-lactone product relative to previous reports. The enantioselectivities obtained varied considerably, even within a group of structurally closely related NHCs. This study demonstrates the challenge of designing NHCs with a general ability to induce asymmetry in a broader range of reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.004
• 作为产物：
  描述：

  L-苯甘氨酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-N1-(2,6-diisopropylphenyl)-N2-(2-hydroxy-1-phenylethyl)oxalamide
  参考文献：
  名称：

  Asymmetric induction afforded by chiral azolylidene N-heterocyclic carbenes (NHC) catalysts

  摘要：

  Screening studies of new chiral imidazolium and triazolium based NHC salts I-VIII as ligands in asymmetric organometallic catalysis and as organocatalysts showed that these catalysts efficiently promoted the reactions. Moderate enantioselectivities (55-57% ee) were obtained in the asymmetric Cu-NHC catalysed conjugate additions of diethylzinc to cyclohexenone, in accordance with most previous studies. The chiral induction afforded in the gold(I)-NHC catalysed cyclopropanation reactions was low (< 28% ee). However, these results represent the first reported chiral gold(I)-NHC catalysed olefin cyclopropanation. The NHC-organocatalysed asymmetric cross-annulation of cinnamaldehyde and trifluoroacetophenone gave lower enantioselectivity (< 50% ee) but higher yields of the gamma-lactone product relative to previous reports. The enantioselectivities obtained varied considerably, even within a group of structurally closely related NHCs. This study demonstrates the challenge of designing NHCs with a general ability to induce asymmetry in a broader range of reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.004