(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methyl isocyanide | 1101195-44-1

• 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 isocyanide
• 英文别名: CN-Gly-OBO；1-(Isocyanomethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 1101195-44-1
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: QSLODNTUTJVENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  32
• 氢给体数：
  0
• 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 isocyanide 、 异丁醛 、 苄胺 、 三氟乙酸 以 甲醇 为溶剂， 以68%的产率得到2-[benzyl-(2,2,2-trifluoroacetyl)amino]-3-methyl-N-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)methyl]butanamide
  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：

  [(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

文献信息

• One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
  作者：Alexander G. Zhdanko、Anton V. Gulevich、Valentine G. Nenajdenko

  DOI：10.1016/j.tet.2009.04.030

  日期：2009.6

  Cys–Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions

  通过Ugi四组分反应，使用各种苄硫基醛和酮作为羰基结构单元，可以合成得到完全保护的天然和非天然N-乙酰半胱氨酸，二肽Cys-Gly，谷胱甘肽和高谷胱甘肽衍生物。研究了该方法的范围和局限性。讨论了在Ugi反应中咪唑啉副产物的形成。在某些反应中，显示2,2,2-三氟乙醇是一种比甲醇更好的反应介质。同样，当异氰基乙酸的更高反应性时，异氰基乙酸的4-甲基-2,6,7-三氧杂双环[2.2.2]辛基衍生物（OBO-酯）被证明比异氰基乙酸乙酯更适合用作肽合成前体。需要异氰酸酯。