tert-butyl (3S,7aR)-7a-methyl-5-oxo-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate | 137303-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: tert-butyl (3S,7aR)-7a-methyl-5-oxo-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate
• CAS: 137303-68-5
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: UGVBFMHJLIKOAW-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,7aR)-7a-methyl-5-oxo-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate 、 2,3-二甲基-1,3-丁二烯 反应 5.0h， 以94%的产率得到tert-butyl (3S,5aR,9aR,9bR)-7,8,9b-trimethyl-5-oxo-3-propan-2-yl-3,6,9,9a-tetrahydro-2H-[1,3]oxazolo[2,3-a]isoindole-5a-carboxylate
  参考文献：
  名称：

  Busacca, Carl A.; Meyers, A. I., Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2299 - 2316

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (3S-顺式)-(+)-2,3-二氢-3-异丙基-7a-甲基吡咯并[2,1-b]噁唑-5(7a h)-酮 生成 tert-butyl (3S,7aR)-7a-methyl-5-oxo-3-propan-2-yl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate
  参考文献：
  名称：

  Busacca, Carl A.; Meyers, A. I., Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2299 - 2316

  摘要：

  DOI：

文献信息

• Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams
  作者：Andrew H. Fray、A. I. Meyers

  DOI：10.1021/jo9600870

  日期：1996.1.1

  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.
• Diastereoselective azomethine ylide cycloadditions to unsaturated, chiral bicyclic lactams
  作者：Andrew H. Fray、A.I. Meyers

  DOI：10.1016/s0040-4039(00)92506-1

  日期：1992.6

  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.