(R)-(+)-trans-4-[(triisopropylsilyl)amino]-2-heptenoic acid ethyl ester | 1006035-98-8

• 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: (R)-(+)-trans-4-[(triisopropylsilyl)amino]-2-heptenoic acid ethyl ester
• CAS: 1006035-98-8
• 化学式: C₁₈H₃₇NO₂Si
• 分子量: 327.583
• InChiKey: HJVIDHQWOGKXEQ-GZKZCVOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-trans-4-[(triisopropylsilyl)amino]-2-heptenoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 以65%的产率得到(R)-(-)-trans-4-amino-2-heptenoic 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：

  (-)-N-(triisopropylsilyl)-D-norvalinaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 反应 12.0h， 以81%的产率得到(R)-(+)-trans-4-[(triisopropylsilyl)amino]-2-heptenoic 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