(+/-)-trans-4-amino-2-pentenoic acid ethyl ester | 959310-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-trans-4-amino-2-pentenoic acid ethyl ester
• 英文别名: Ethyl (2E)-4-aminopent-2-enoate；ethyl (E)-4-aminopent-2-enoate
• CAS: 959310-41-9
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: LVQXQSJXFIEHAZ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-4-amino-2-pentenoic acid ethyl ester 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (R)-trans-4-[((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)amino]-2-pentenoic acid ethyl ester 、 (S)-trans-4-[((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)amino]-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993
• 作为产物：
  描述：

  (+/-)-trans-4-[(triisopropylsilyl)amino]-2-pentenoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (+/-)-trans-4-amino-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993

文献信息

• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.