cyclopropylidenemethanone | 59078-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopropylidenemethanone
• 英文别名: cyclopropylidene ketene；carbonylcyclopropane；Dimethylenketen；Ethyleneketene；Carbonylcyclopropan；Methanone, cyclopropylidene-
• CAS: 59078-44-3
• 化学式: C₄H₄O
• 分子量: 68.0752
• InChiKey: IDITVISEENJSMD-UHFFFAOYSA-N

物化性质

• 沸点：
  49.0±7.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclopropylidenemethanone 生成 Dispiro[2,1,2,1]octan-4,8-dion
  参考文献：
  名称：

  HOFFMANN, H. M. R.;WULFF, J. M.;KUETZ, A.;WARTCHOW, R., ANGEW. CHEM., 1982, 94, N 1, 79-80

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-环丙烷二甲酸环异亚丙酯 生成 cyclopropylidenemethanone
  参考文献：
  名称：

  环亚丙基甲酮：一种准对称分子

  摘要：

  环亚丙基甲酮结构分析练习曲，微量分光镜，开发行星分子和原子结构问题

  DOI：

  10.1021/ja00337a012

文献信息

• Bock, Hans; Hirabayashi, Takakuni; Mohmand, Shamsher, Chemische Berichte, 1981, vol. 114, # 7, p. 2595 - 2608
  作者：Bock, Hans、Hirabayashi, Takakuni、Mohmand, Shamsher

  DOI：——

  日期：——
• Sind pyrazolin-3,5-dione als vorstufen für carbene geeignet ?
  作者：Günther Maier、Marc Heider、Claudia Sierakowski

  DOI：10.1016/0040-4039(91)85012-t

  日期：1991.4

  Thermolysis of the 1-pyrazoline-3,5-diones 3a,b yields the ketenes 4a,b. Upon matrix irradiation of 3a,b a second molecule of CO is eliminated under formation of the carbenes 5a,b, which finally lead to propene (6) or allene (7).
• Photolysis of Matrix Isolated Cyclopropylidene Ketene: Kinetic and Theoretical Studies of the Cyclopropylidene Formation
  作者：Maurice Monnier、Alain Allouche、Patrick Verlaque、Jean-Pierre Aycard

  DOI：10.1021/j100016a038

  日期：1995.4

  Cyclopropylidene ketene 2 is generated by ultraviolet irradiation (lambda greater than or equal to 230 nm) of cyclopropanecarbonyl chloride isolated in argon matrices at 15 K. FT-IR spectra of the primary photolysis products (2 and HCl) trapped in the same cage show the formation of molecular complexes. The HCl stretching mode observed at 2793.5, 2739 cm(-1) is shifted to 61 cm(-1) below the frequency of monomeric HCl (2888.0, 2863.5 cm(-1)) in argon matrix. Irradiation of 2 at lambda greater than or equal to 230 nm induces reversible formation of CO and of a new transient assumed to be cyclopropylidene 3. This carbene reacts with HCl trapped in the same cage or gives 1,2-propadiene by intramolecular rearrangement. The kinetic data show that the rate constant of 1,2-propadiene formation is twice as large as that of cyclopropyl chloride formation. To account for the results of matrix isolation experiments the photodissociation of the cyclopropylidene ketene was modeled by ab initio calculation using 6.31G* and ''mini'' Huzinaga basis sets.
• Unsaturated ketenes: A study of their formation and rearrangement by tandem mass spectrometry and low-temperature infrared spectroscopy
  作者：André Maquestiau、Pascal Pauwels、Robert Flammang、Primož Lorenčak、Curt Wentrup

  DOI：10.1002/oms.1210210505

  日期：1986.5

  AbstractA combination of collisional activation mass spectrometry and low‐temperature infrared spectroscopy has been used to monitor the production and isomerization of vinyl‐ and methylene‐ketenes. Vinyl‐ and 2‐propenyl‐ketenes were produced by flash vacuum pyrolysis of β,γ‐unsaturated acid chlorides. Vinyl(carboxyl)ketenes, vinylketenes and methyleneketenes were obtained from Meldrum's acid derivatives (5‐alkylidene‐1,3‐dioxane‐4,6‐diones). The formation of methyleneketenes by pyrolysis of α, β‐unsaturated acid chlorides is only indicated in the mass spectrometry experiments. Carbonylcyclopropane was obtained by pyrolysis of cyclopropylcarbonyl chloride or the corresponding Meldrum's acid derivative. The methyleneketenes isomerize to vinylketenes in the gas phase, particularly under conditions involving long contact times. Carbonylcyclopropane thermally decarbonylates to allene, not methylacetylene. Molecular ions of vinylketenes are obtained via pyrolysis of either acid chlorides or Meldrum's acid derivatives. Molecular ions of alkylmethyleneketenes are obtained pure only by electron impact induced fragmentation of Meldrum's acid derivatives.