methyl (R)-2-(9-fluorenylmethoxycarbonyl)amino-4-pentenoate | 225656-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (R)-2-(9-fluorenylmethoxycarbonyl)amino-4-pentenoate
• 英文别名: methyl (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pent-4-enoate；methyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-enoate
• CAS: 225656-31-5
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: BCAQZXPPJIDARV-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  D-烯丙基甘氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl (R)-2-(9-fluorenylmethoxycarbonyl)amino-4-pentenoate
  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

• Novel B1 bradykinin receptor antagonists
  申请人：Askew Benny C.

  公开号：US20080249106A1

  公开（公告）日：2008-10-09

  The invention encompasses novel compounds and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for treatment of diseases mediated by B1 bradykinin receptor.

  这项发明涵盖了新型化合物及其药物可接受的衍生物、药物组合物以及治疗由B1布雷金因子受体介导的疾病的方法。
• 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.