N-benzyl-2-cyclohexylideneacetamide | 853063-80-6

• 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-benzyl-2-cyclohexylideneacetamide
• CAS: 853063-80-6
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: BELRFCOLPDPEFR-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  439.6±28.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-cyclohexylideneacetamide 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， 生成 N-benzyl-2-cyclohexylidene-1-ethanamine
  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：

  环己烷亚基乙酸乙酯 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-benzyl-2-cyclohexylideneacetamide
  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

文献信息

• Aminocarbonylations of alkenyl phosphates, chlorides, bromides, and triflates with Mo(CO)6 as a solid CO source
  作者：Olof Lagerlund、Mette L.H. Mantel、Mats Larhed

  DOI：10.1016/j.tet.2009.06.101

  日期：2009.9

  Palladium-catalyzed aminocarbonylations of alkenyl chlorides, bromides, and triflates were investigated using Mo(CO)6 as a solid carbon monoxide source. The reactions afforded moderate to good yields producing a wide variety of acrylamides after 20 min of microwave irradiation. In addition, the aminocarbonylation reaction was, for the first time, expanded to include alkenyl phosphates as starting materials

  使用Mo（CO）6作为固体一氧化碳源，研究了烯基氯化物，溴化物和三氟甲磺酸酯的钯催化的氨基羰基化反应。在微波照射20分钟后，反应可提供中等至良好的收率，可生产出多种丙烯酰胺。另外，氨基羰基化反应首次扩大到包括链烯基磷酸酯作为起始原料。
• Convenient Synthesis of Substituted Piperidinones from α,β-Unsaturated Amides:  Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine
  作者：Kiyosei Takasu、Naoko Nishida、Akiko Tomimura、Masataka Ihara

  DOI：10.1021/jo050261x

  日期：2005.5.1

  An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.