(R)-methyl 2-isopropyl-4,5-dihydrooxazole-4-carboxylate | 1414648-98-8

• 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: (R)-methyl 2-isopropyl-4,5-dihydrooxazole-4-carboxylate
• 英文别名: methyl (4R)-2-propan-2-yl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 1414648-98-8
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: XCOCYBLYCISXHZ-ZCFIWIBFSA-N

物化性质

• 沸点：
  214.7±33.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-isopropyl-4,5-dihydrooxazole-4-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以63%的产率得到(S)-(2-isopropyl-4,5-dihydrooxazol-4-yl)methanol
  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：

  异丁酰胺 、 D-丝氨酸甲酯盐酸盐 在 triethyloxonium fluoroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以67%的产率得到(R)-methyl 2-isopropyl-4,5-dihydrooxazole-4-carboxylate
  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