2-amino-3-cyano-2-penten-4-one | 1113-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3-cyano-2-penten-4-one
• 英文别名: 4-amino-3-cyano-3-penten-2-one；2-Amino-3-cyano-penten-(2)-on-(4)；2-Amino-3-cyano-pent-2-en-4-on；2-Amino-3-cyano-pent-4-on-2-en；2-acetyl-3-aminobut-2-enenitrile
• CAS: 1113-72-0
• 化学式: C₆H₈N₂O
• mdl: MFCD18834754
• 分子量: 124.142
• InChiKey: RDRVJVHEWGXCLC-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  347.0±32.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-cyano-2-penten-4-one 在 sodium hydroxide 作用下， 生成 3-cyanoacetylacetone
  参考文献：
  名称：

  Reactions of methylaluminium compounds with acetonitrile

  摘要：

  DOI：

  10.1016/s0022-328x(00)85635-1
• 作为产物：
  描述：

  2-乙酰基-3-氧代丁腈 在 ammonium hydroxide 作用下， 反应 2.0h， 以58%的产率得到2-amino-3-cyano-2-penten-4-one
  参考文献：
  名称：

  Vibrational assignment and structure of 4-amino-3-cyano-3-penten-2-one

  摘要：

  Fourier transform infrared and Fourier transform Raman spectra of 4-amino-3-cyano-3-penten-2-one and its deuterated analogue have been obtained. Density functional theory (DFT) B3LYP and G96LYP calculations have been carried out with the purpose of understanding the vibrational spectra of this compound and its deuterated analogue. Vibrational wavenumbers calculated by B3LYP/6-31G* (with a p shell added on the amine protons) force field are closed with the experimental results. The percentage of deviation of the bond lengths and bond angles gives a good picture of the normal modes, and serves as a basis for the assignment of the wavenumbers. The calculated geometrical parameters show a strong intramolecular hydrogen bond with a N...O distance of 2.605-2.622 Angstrom. This bond length is about 0.04-0.06 Angstrom shorter than that in its parent, 4-amino-3-penten-2-one (with no cyano substitution in the alpha-position). Experimental evidences also indicate presence of an intermolecular hydrogen bond in the solid state, completely, and in solution, partially. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00179-5

文献信息

• Yagupol'skii, L. M.; Matyushecheva, G. I.; Pavlenko, N. V., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 10 - 14
  作者：Yagupol'skii, L. M.、Matyushecheva, G. I.、Pavlenko, N. V.、Boiko, V. N.

  DOI：——

  日期：——
• Reactions of methylaluminium compounds with acetonitrile
  作者：W. Kuran、S. Pasynkiewicz、A. Salek

  DOI：10.1016/s0022-328x(00)85635-1

  日期：1974.7
• Vibrational assignment and structure of 4-amino-3-cyano-3-penten-2-one
  作者：Haydar Raissi、Sayyed Faramarz Tayyari、Fariba Tayyari

  DOI：10.1016/s0022-2860(02)00179-5

  日期：2002.8

  Fourier transform infrared and Fourier transform Raman spectra of 4-amino-3-cyano-3-penten-2-one and its deuterated analogue have been obtained. Density functional theory (DFT) B3LYP and G96LYP calculations have been carried out with the purpose of understanding the vibrational spectra of this compound and its deuterated analogue. Vibrational wavenumbers calculated by B3LYP/6-31G* (with a p shell added on the amine protons) force field are closed with the experimental results. The percentage of deviation of the bond lengths and bond angles gives a good picture of the normal modes, and serves as a basis for the assignment of the wavenumbers. The calculated geometrical parameters show a strong intramolecular hydrogen bond with a N...O distance of 2.605-2.622 Angstrom. This bond length is about 0.04-0.06 Angstrom shorter than that in its parent, 4-amino-3-penten-2-one (with no cyano substitution in the alpha-position). Experimental evidences also indicate presence of an intermolecular hydrogen bond in the solid state, completely, and in solution, partially. (C) 2002 Elsevier Science B.V. All rights reserved.