methyl (3S,7aS)-5-oxo-7a-phenyl-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate | 143140-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (3S,7aS)-5-oxo-7a-phenyl-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate
• CAS: 143140-05-0
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: POOZEEXOCLFXQY-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-甲氧基甲基-N-(三甲基甲硅基)甲基-1-苯乙胺 、 methyl (3S,7aS)-5-oxo-7a-phenyl-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate 在 三氟乙酸 作用下， 生成 methyl (1S,2S,5S,8S)-7-oxo-2-phenyl-10-[(1R)-1-phenylethyl]-5-propan-2-yl-3-oxa-6,10-diazatricyclo[6.3.0.02,6]undecane-8-carboxylate 、
  参考文献：
  名称：

  Diastereoselective azomethine ylide cycloadditions to unsaturated, chiral bicyclic lactams

  摘要：

  The levels of diastereoselection resulting from the 1,3-dipolar cycloaddition of chiral and achiral azomethine ylides 2(a-c) to chiral, unsaturated bicyclic lactams 1(a-f) are described in terms of steric factors.

  DOI：

  10.1016/s0040-4039(00)92506-1
• 作为产物：
  描述：

  (3S-顺式)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]恶唑-5(6H)-酮 、 氯甲酸甲酯 生成 methyl (3S,7aS)-5-oxo-7a-phenyl-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate
  参考文献：
  名称：

  Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams

  摘要：

  Double diastereoselectivity data were analyzed to provide insight into the structural features that influence pi-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (Delta Delta G(double dagger)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R(2)) and concave faces of the bicyclic lactams. This effectively hindered both alpha- and beta-approaches in the nonextended transition states shown in Figure 1. The second major steric interaction was provided by the nonbonded interactions (i) between the R(1) angular substituent on the bicyclic lactam and the pi-system of the dipole as shown in Figures 3 and 4. This interaction was shown to be very significant, causing reversal in pi-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.

  DOI：

  10.1021/jo9600870