(4R,5S)-isopropyl 5-benzamido-5-methyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate | 1309576-39-3

• 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: (4R,5S)-isopropyl 5-benzamido-5-methyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate
• 英文别名: propan-2-yl (4R,5S)-5-benzamido-5-methyl-6-oxo-4-phenyl-4H-pyran-2-carboxylate
• CAS: 1309576-39-3
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: RXXQDMKDFFHKGH-JPYJTQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基-2-苯基-2-噁唑啉-5-酮 、 isopropyl (E)-2-oxo-4-phenylbut-3-enoate 在 4-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(naphthalen-1-ylmethoxy)methyl]quinolin-6-ol 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以92%的产率得到(4R,5S)-isopropyl 5-benzamido-5-methyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate
  参考文献：
  名称：

  Bifunctional cinchona alkaloids-catalyzed asymmetric [4+2] cycloaddition reaction of β,γ-unsaturated α-keto esters with oxazolones

  摘要：

  A highly enantioselective [4+2] cycloaddition reaction of beta,gamma-unsaturated alpha-keto esters with oxazolones was realized with readily available cinchona alkaloids as the catalysts. Using this reaction, a series of highly functionalized delta-lactones with adjacent alpha-quaternary-beta-tertiary stereocenters were obtained in high yields (up to 97%) and with good-to-excellent enantioselectivities (up to 97% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.069