N-Adamantan-1-yl-2-cyclohexylidene-2-fluoro-acetamide | 777946-31-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-Adamantan-1-yl-2-cyclohexylidene-2-fluoro-acetamide
• 英文别名: N-(1-adamantyl)-2-cyclohexylidene-2-fluoroacetamide
• CAS: 777946-31-3
• 化学式: C₁₈H₂₆FNO
• 分子量: 291.409
• InChiKey: IEGHJUWIQFRXJB-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±41.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-Adamantan-1-yl-2-cyclohexylidene-2-fluoro-acetamide 在 三氯氧磷 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 4.0h， 以94%的产率得到Adamantan-1-yl-(2-cyclohexylidene-2-fluoro-ethyl)-amine
  参考文献：
  名称：

  Fluoro-Olefins as Peptidomimetic Inhibitors of Dipeptidyl Peptidases

  摘要：

  The feasibility of the fluoro-olefin function as a peptidomimetic group in inhibitors for dipeptidyl peptidase IV and II (DPP IV and DPP II) is investigated by evaluation of N-substituted Gly-Psi[CF=C]pyrrolidines, Gly-Psi[CF=C]piperldines, and Gly-Psi[CF=C](2-cyano)pyrrolidines. Of this later class, the (Z)- and (E)-fluoro-olefin analogues were prepared and chemical stability in comparison with the parent amide was checked. Most of these compounds exhibited a strong binding preference toward DPP II with IC50 values in the low micromolar range, while only low DPP IV inhibitory potential is seen.

  DOI：

  10.1021/jm0495982
• 作为产物：
  描述：

  ethyl 2-cyclohexylidene-2-fluoroacetate 在 氢氧化钾 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.08h， 生成 N-Adamantan-1-yl-2-cyclohexylidene-2-fluoro-acetamide
  参考文献：
  名称：

  Fluoro-Olefins as Peptidomimetic Inhibitors of Dipeptidyl Peptidases

  摘要：

  The feasibility of the fluoro-olefin function as a peptidomimetic group in inhibitors for dipeptidyl peptidase IV and II (DPP IV and DPP II) is investigated by evaluation of N-substituted Gly-Psi[CF=C]pyrrolidines, Gly-Psi[CF=C]piperldines, and Gly-Psi[CF=C](2-cyano)pyrrolidines. Of this later class, the (Z)- and (E)-fluoro-olefin analogues were prepared and chemical stability in comparison with the parent amide was checked. Most of these compounds exhibited a strong binding preference toward DPP II with IC50 values in the low micromolar range, while only low DPP IV inhibitory potential is seen.

  DOI：

  10.1021/jm0495982