methyl (2S)-1-benzyl-2-(2-methylbut-3-en-2-yl)pyrrolidine-2-carboxylate | 229964-77-6

• 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: methyl (2S)-1-benzyl-2-(2-methylbut-3-en-2-yl)pyrrolidine-2-carboxylate
• CAS: 229964-77-6
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: BXHADQRBFVFSHZ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-benzyl-2-(2-methylbut-3-en-2-yl)pyrrolidine-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以57%的产率得到N-benzyl-2-(1,1-dimethylallyl)prolinol
  参考文献：
  名称：

  Chirality Transfer from Carbon to Nitrogen to Carbon via Cyclic Ammonium Ylides

  摘要：

  Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon treatment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderate to complete stereospecificity. The overall process entails chirality transfer from the original alpha carbon to the neighboring nitrogen and then back to the carbon.

  DOI：

  10.1021/ol9905349
• 作为产物：
  描述：

  N-benzyl-(S)-proline methyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 methyl (2S)-1-benzyl-2-(2-methylbut-3-en-2-yl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chirality Transfer from Carbon to Nitrogen to Carbon via Cyclic Ammonium Ylides

  摘要：

  Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon treatment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderate to complete stereospecificity. The overall process entails chirality transfer from the original alpha carbon to the neighboring nitrogen and then back to the carbon.

  DOI：

  10.1021/ol9905349

文献信息

• Chirality Transfer from Carbon to Nitrogen to Carbon via Cyclic Ammonium Ylides
  作者：Kevin W. Glaeske、F. G. West

  DOI：10.1021/ol9905349

  日期：1999.7.1

  Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon treatment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderate to complete stereospecificity. The overall process entails chirality transfer from the original alpha carbon to the neighboring nitrogen and then back to the carbon.