1-(9-fluorenylmethyl) 2-methyl (2R,4R)-4-formyloxy-1,2-piperidinedicarboxylate | 225656-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1-(9-fluorenylmethyl) 2-methyl (2R,4R)-4-formyloxy-1,2-piperidinedicarboxylate
• 英文别名: 1-O-(9H-fluoren-9-ylmethyl) 2-O-methyl (2R,4R)-4-formyloxypiperidine-1,2-dicarboxylate
• CAS: 225656-39-3
• 化学式: C₂₃H₂₃NO₆
• 分子量: 409.439
• InChiKey: BRZNQOVFRXNMIJ-QVKFZJNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(9-fluorenylmethyl) 2-methyl (2R,4R)-4-formyloxy-1,2-piperidinedicarboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions

  摘要：

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a
• 作为产物：
  描述：

  聚合甲醛 、 甲酸 、 methyl (R)-2-(9-fluorenylmethoxycarbonyl)amino-4-pentenoate 反应 16.0h， 以43%的产率得到1-(9-fluorenylmethyl) 2-methyl (2R,4S)-4-formyloxy-1,2-piperidinedicarboxylate
  参考文献：
  名称：

  Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions

  摘要：

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a

文献信息

• Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions
  作者：Floris P. J. T. Rutjes、Johan J. N. Veerman、Wim J. N. Meester、Henk Hiemstra、Hans E. Schoemaker

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a

  日期：1999.5

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.