N-[2-methyl-1-[[(1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)butyl]amino]-1-oxopropan-2-yl]-N-[(1S)-1-phenylethyl]benzamide | 1101195-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-methyl-1-[[(1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)butyl]amino]-1-oxopropan-2-yl]-N-[(1S)-1-phenylethyl]benzamide
• CAS: 1101195-60-1
• 化学式: C₃₀H₄₀N₂O₅
• 分子量: 508.658
• InChiKey: LZHWCOMLVOBPKO-WQTJTDHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl isocyanide 、 (S)-(-)- α-甲基苄胺 、 丙酮 、 苯甲酸 以 甲醇 为溶剂， 以46%的产率得到N-[2-methyl-1-[[(1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)butyl]amino]-1-oxopropan-2-yl]-N-[(1S)-1-phenylethyl]benzamide
  参考文献：
  名称：

  Nonracemizable Isocyanoacetates for Multicomponent Reactions

  摘要：

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.

  DOI：

  10.1021/jo802420c

文献信息

• Nonracemizable Isocyanoacetates for Multicomponent Reactions
  作者：Alexander G. Zhdanko、Valentine G. Nenajdenko

  DOI：10.1021/jo802420c

  日期：2009.1.16

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.