[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl]formamide | 1101195-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl]formamide
• 英文别名: OHCNH-Gly-OBO；N-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)methyl]formamide
• CAS: 1101195-37-2
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: JGVVYIOBGVMANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl]formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl isocyanide
  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
• 作为产物：
  描述：

  1-(aminomethyl)-4-methyl-2,6,7-trioxabiyclo[2,2,2]octane 、 甲酸乙酯 以81%的产率得到[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl]formamide
  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.