ethyl (4R,5S)-5-(benzamido)-5,6-dihydro-5-methyl-6-oxo-4-phenyl-4H-pyran-2-carboxylate | 1309576-38-2

• 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: ethyl (4R,5S)-5-(benzamido)-5,6-dihydro-5-methyl-6-oxo-4-phenyl-4H-pyran-2-carboxylate
• 英文别名: (4R,5S)-ethyl 5-benzamido-5-methyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate；ethyl (4R,5S)-5-benzamido-5-methyl-6-oxo-4-phenyl-4H-pyran-2-carboxylate
• CAS: 1309576-38-2
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: CEIHSTSQLGOMSG-VGSWGCGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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 、 (E)-ethyl-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90%的产率得到ethyl (4R,5S)-5-(benzamido)-5,6-dihydro-5-methyl-6-oxo-4-phenyl-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

文献信息

• Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base
  作者：Masahiro Terada、Hiroyuki Nii

  DOI：10.1002/chem.201003015

  日期：2011.2.7

  cycloaddition reaction of azlactones with β,γ‐unsaturated α‐ketoesters was demonstrated by taking advantage of the multiple reactive sites on the azlactone with the use of an axially chiral guanidine‐base catalyst. The most likely reaction pathway involves three consecutive steps to provide a facile access to α‐amino δ‐lactones with a sugar framework in a highly stereoselective manner (see scheme).

  甜蜜的催化！利用轴向手性胍基催化剂，通过利用氮杂内酯上的多个反应位点，证明了氮杂内酯与β，γ-不饱和α-酮酸酯的对映体和非对映选择性环加成反应。最可能的反应途径包括三个连续的步骤，以高度立体选择性的方式（使用方案）轻松获得带有糖骨架的α-氨基δ-内酯。