(E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylhex-3-enoic acid | 134210-55-2

• 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: (E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylhex-3-enoic acid
• CAS: 134210-55-2
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: GEIOHWYTDLTYRM-IAYMVZNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 (E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylhex-3-enoic acid 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以63%的产率得到methyl (2S)-2-[[(E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylhex-3-enoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010
• 作为产物：
  描述：

  [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl]-carbamic acid tert-butyl ester 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢氟酸 、 sodium carbonate 、 臭氧 、 苯甲醚 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 107.42h， 生成 (E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-propan-2-ylhex-3-enoic acid
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010