2-cyano-N-methyl-5-phenylpent-2-en-4-ynamide

• 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: 2-cyano-N-methyl-5-phenylpent-2-en-4-ynamide
• 英文别名: (E)-2-cyano-N-methyl-5-phenylpent-2-en-4-ynamide；2-cyano-5-phenyl-pent-2-en-4-ynoic acid N-methylamide form (I)
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: BMJRZIXJUVEJHR-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙炔醛 、 2-氰基-N-甲基乙酰胺 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以95%的产率得到2-cyano-N-methyl-5-phenylpent-2-en-4-ynamide
  参考文献：
  名称：

  由β-酮酰胺和ynals无过渡金属高效合成2-吡啶酮

  摘要：

  开发了一种方便而有效的环化反应，以良好的产率获得了2-吡啶酮。多种取代的β-酮酰胺和ynal具有良好的耐受性，尤其是在无过渡金属的条件下，该转化产生的水仅作为副产物。此外，从β-氰基酰胺和ynals以高收率获得了共轭烯炔酰胺。

  DOI：

  10.1016/j.tetlet.2019.04.001

文献信息

• Conformational polymorphs of 22-cyano-<i>N</i>-methyl-5-phenylpent-2-en-4-ynamide
  作者：Oleg Ya. Borbulevych、Igor R. Golding、Alexander N. Shchegolikhin、Zinaida S. Klemenkova、Mikhail Yu. Antipin

  DOI：10.1107/s010827010100909x

  日期：2001.8.15

  Although the two polymorphic modifications, (I) and (II), of the title compound, C13H10N2O, crystallize in the same space group (P2(1)/c), their asymmetric units have Z' values of 1 and 2, respectively. These are conformational polymorphs, since the molecules in phases (I) and (II) adopt different rotations of the phenyl ring with respect the central 2-cyanocarboxy-aminoprop-2-enyl fragment. Calculations of crystal packing using Cerius(2) [Molecular Simulations (1999). 9685 Scranton Road, San Diego, CA 92121, USA] have shown that (I) is more stable than (II), by 1.3 kcal mol(-1) for the crystallographically determined structures and by 1.56 kcal mol(-1) for the optimized structures (1 kcal mol(-1) = 4.184 kJ mol(-1)). This difference is mainly attributed to the different strengths of the hydrogen bonding in the two forms.
• Transition-metal-free highly efficient synthesis of 2-pyridones from β-keto amides and ynals
  作者：Zhengwang Chen、Jiayang Liu、Caiju Jin、Qi Tan、Min Ye

  DOI：10.1016/j.tetlet.2019.04.001

  日期：2019.5

  A convenient and efficient annulation reaction was developed, affording 2-pyridones in good to excellent yields. A variety of substituted β-keto amides and ynals were well tolerated, and especially the transformation produced water as only by-product under transition-metal-free conditions. Furthermore, the conjugated enyneamides were achieved from β-cyano amides and ynals in high yields.

  开发了一种方便而有效的环化反应，以良好的产率获得了2-吡啶酮。多种取代的β-酮酰胺和ynal具有良好的耐受性，尤其是在无过渡金属的条件下，该转化产生的水仅作为副产物。此外，从β-氰基酰胺和ynals以高收率获得了共轭烯炔酰胺。