(3S,4R)-3-(1-benzyl-4-vinyl-pyrrolidin-3-yl) 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 912969-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-3-(1-benzyl-4-vinyl-pyrrolidin-3-yl) 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: [(3S,4R)-1-benzyl-4-ethenylpyrrolidin-3-yl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 912969-49-4
• 化学式: C₂₁H₃₀N₂O₃
• 分子量: 358.481
• InChiKey: RKIAOGXBYKUTBW-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-(1-benzyl-4-vinyl-pyrrolidin-3-yl) 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 甲醇 、 甲烷磺酸 、 potassium carbonate 作用下， 反应 21.0h， 以56%的产率得到(3S,4R)-1-benzyl-4-vinylpyrrolidin-3-ol
  参考文献：
  名称：

  Asymmetric Synthesis of 3-Hydroxy-pyrrolidines via Tin−Lithium Exchange and Cyclization

  摘要：

  We report a method for the synthesis of chiral pyrrolidines using tin-lithium exchange and cyclization reactions. The precursors are formed readily from simple starting materials and undergo tin-lithium exchange by treatment with n-butyllithium. Subsequent intramolecular carbolithiation is stereoselective to give highly enantiomerically enriched pyrrolidines in excellent yields.

  DOI：

  10.1021/ol061615p
• 作为产物：
  描述：

  [1S,2(2E)]-2-(N-benzyl-N-(4-chlorobut-2-enyl)-amino)-1-tributylstannylethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以95%的产率得到(3S,4R)-3-(1-benzyl-4-vinyl-pyrrolidin-3-yl) 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of 3-Hydroxy-pyrrolidines via Tin−Lithium Exchange and Cyclization

  摘要：

  We report a method for the synthesis of chiral pyrrolidines using tin-lithium exchange and cyclization reactions. The precursors are formed readily from simple starting materials and undergo tin-lithium exchange by treatment with n-butyllithium. Subsequent intramolecular carbolithiation is stereoselective to give highly enantiomerically enriched pyrrolidines in excellent yields.

  DOI：

  10.1021/ol061615p

文献信息

• Asymmetric Synthesis of 3-Hydroxy-pyrrolidines via Tin−Lithium Exchange and Cyclization
  作者：Guido Christoph、Christian Stratmann、Iain Coldham、Dieter Hoppe

  DOI：10.1021/ol061615p

  日期：2006.9.1

  We report a method for the synthesis of chiral pyrrolidines using tin-lithium exchange and cyclization reactions. The precursors are formed readily from simple starting materials and undergo tin-lithium exchange by treatment with n-butyllithium. Subsequent intramolecular carbolithiation is stereoselective to give highly enantiomerically enriched pyrrolidines in excellent yields.