(1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl isocyanide | 1101195-49-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl isocyanide
• 英文别名: CN-Ile-OBO；1-[(1S,2S)-1-isocyano-2-methylbutyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 1101195-49-6
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: JGICUGXYGZTWDY-JYBOHDQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl isocyanide 在 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 28.17h， 生成
  参考文献：
  名称：

  The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity

  摘要：

  The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

  DOI：

  10.1021/ja2022027
• 作为产物：
  描述：

  (1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylformamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,2S)-2-methyl-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl 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