| 139449-09-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 139449-09-5；139560-39-7
• 化学式: C₂₂H₃₁N₃O₆
• 分子量: 433.505
• InChiKey: BGXSRORDDYWAKU-UBFHEZILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  126.75
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 N-Boc-L-苯丙氨醛 、 L-谷氨酸二甲酯盐酸盐 在 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Ψ[CH（CN）NH]假肽的合成。新的肽键替代

  摘要：

  在存在的情况下，通过路易斯酸催化的N保护的α-氨基醛与C保护的氨基酸或肽的反应，一种简单而通用的通用方法来制备新的肽键替代物（[CH（CN）NH]描述了TMSCN的专利。

  DOI：

  10.1016/0040-4039(91)80539-i

文献信息

• Studies on the synthesis of cyanomethyleneamino pseudopeptides
  作者：Rosario Herranz、M. Luisa Suarez-Gea、Soledad Vinuesa、M. Teresa Garcia-Lopez

  DOI：10.1021/jo00071a031

  日期：1993.9

  Various cyanomethyleneamino pseudodipeptides were easily prepared in high yield by the Lewis acid catalyzed addition of trimethylsilyl cyanide to unstable aldimine intermediates, obtained from the reaction of N-protected alpha-amino aldehydes with C-protected amino acids. The two possible (R)- and (S)-epimers at the peptide bond surrogate chiral center were obtained. In this thermodynamically controlled synthesis, the absolute configurations of the alpha-amino aldehyde and the amino acid proved to be the main factors determining its stereoselectivity. The new N-Boc- and N-Z-protected pseudodipeptides were deblocked under standard conditions. In spite of the lability of the new peptide bond surrogate psi[CH(CN)NH] in basic medium, high yields of C-deprotected pseudodipeptides were obtained by controlling the saponification conditions of the methyl esters. The use of free alpha-amino acids in the modified Strecker synthesis reported here can be employed as an alternative for the synthesis of C-deprotected cyanomethyleneamino pseudopeptides. The N- or C-elongation of these pseudodipeptides via the DCC method led to the corresponding psi[CH(CN)NH] pseudotripeptides in high yield.