Methylcyanoketene | 57681-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Methylcyanoketene
• CAS: 57681-10-4
• 化学式: C₄H₃NO
• 分子量: 81.0739
• InChiKey: GGCNOXNIZSYRAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methylcyanoketene 生成 2-Phenalen-(1Z)-ylidene-propionitrile
  参考文献：
  名称：

  NEIDLEIN R.; CEPERA K. F., CHEM. BER., 1978, 111, NO 5, 1824-1832

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Azido-5-tert-butyl-2-cyano-2-methylcyclopent-4-ene-1,3-dione 生成 Methylcyanoketene
  参考文献：
  名称：

  MOORE H. W.; WILBUR D. S., J. ORG. CHEM., 1980, V. 45, NO 22, 4483-4491

  摘要：

  DOI：

文献信息

• Cyanoketenes. Mechanism of tert-butylcyanoketene cycloaddition to aldo- and ketoketenes
  作者：Harold W. Moore、D. Scott Wilbur

  DOI：10.1021/jo01310a042

  日期：1980.10
• Protonated Forms of Iminopropadienones, RN:C:C:C:O, and Cyanoketenes: Combined ab initio MO and Mass Spectrometry Studies
  作者：Robert Flammang、Yves Van Haverbeke、Ming Wah Wong、Andreas Ruehmann、Curt Wentrup

  DOI：10.1021/j100069a008

  日期：1994.5

  The structures and unimolecular fragmentation reactions of protonated iminopropadienones, RN=C=C=C=O (R=H and CH3), were investigated by a combination of mass spectrometry based experiments (collisional activation (CA), neutralization-reionization (NR), and chemical ionization (CI) mass spectrometry and flash vacuum pyrolysis) and high-level ad initio molecular orbital calculations, at the QCISD(T)/6-311+G(2d,p) level of theory. The C- and N-protonated forms, RN(+)=C-CH=C=O and R(HN+=C=C=O, were separately generated from a variety of precursors. The experiments and calculations indicate that the most favorable site of protonation of iminopropadienones is the central carbon atom (C-2), and the resulting ions are best regarded as N-alkylated or N-protonated cyanoketenes. The N-protonated iminopropadienone is close in energy to the C-protonated one, while the O-protonated form is significantly higher in energy. The proton affinities (298 K) of HNCCCO, CH3NCCCO, NCCECO, and NCC(CH3)CO are predicted to be 861, 920, 784, and 798 kJ mol(-1), respectively.
• MOORE H. W.; WILBUR D. S., J. ORG. CHEM., 1980, V. 45, NO 22, 4483-4491
  作者：MOORE H. W.、 WILBUR D. S.

  DOI：——

  日期：——
• NEIDLEIN R.; CEPERA K. F., CHEM. BER., 1978, 111, NO 5, 1824-1832
  作者：NEIDLEIN R.、 CEPERA K. F.

  DOI：——

  日期：——