亚甲基环丙烯 | 4095-06-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 亚甲基环丙烯
• 英文名称: Methylenecyclopropene
• 英文别名: 3-methylene-cyclopropene；3-methylidenecyclopropene
• CAS: 4095-06-1
• 化学式: C₄H₄
• 分子量: 52.0758
• InChiKey: GOSMMPKSWSOPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-methylidene-2-(phenylsulfinyl)cyclopropane 生成 亚甲基环丙烯
  参考文献：
  名称：

  Neue wege zum cyclobutadien und methylencyclopropen

  摘要：

  DOI：

  10.1016/s0040-4039(01)91402-9

文献信息

• Synthese von Triafulven-Vorstufen für<i>Retro</i>-<i>Diels</i>-<i>Alder</i>-Reaktionen
  作者：Jürg Krebs、Dominik Guggisberg、Urs Stämpfli、Markus Neuenschwander

  DOI：10.1002/hlca.19860690410

  日期：1986.6.18

  Synthesis of Triafulvene Precursors for Retro-Diels-Alder Reactions

  Retro - Diels - Alder反应的三氟戊烯前体的合成。
• Synthesis of methylenecyclopropene
  作者：W. E. Billups、Long Jin Lin、Edward W. Casserly

  DOI：10.1021/ja00324a064

  日期：1984.6

  Synthese et caracterisation du methylene cyclopropene a partir du dichloromethylene et de l'allene

  Synthese et caracterisation du 亚甲基环丙烯 a partir du dichloromethylene et de l'allene
• A new methylenecyclopropene synthesis and the isolation of a novel methylenecyclopropene dimer
  作者：W.E Billups、Christoph Gesenberg、Roger Cole

  DOI：10.1016/s0040-4039(97)00085-3

  日期：1997.2

  elimination of trimethylsilylbromide from either cis or trans-1-methylene-2-bromo-3-trimethylsilylcyclopropane over solid cesium fluoride using the vacuum gas-solid reaction procedure yields methylenecyclopropene.

  使用真空气固反应方法在固体氟化铯上从顺式或反式-1-亚甲基-2-溴-3-三甲基甲硅烷基环丙烷中消除三甲基甲硅烷基溴化物，得到亚甲基环丙烯。
• A flow tube study of ion-molecule reactions of acetylene
  作者：J. S. Knight、C. G. Freeman、M. J. McEwan、V. G. Anicich、W. T. Huntress

  DOI：10.1021/j100298a033

  日期：1987.7
• Crossed‐beam reaction of carbon atoms with hydrocarbon molecules. II. Chemical dynamics of <i>n</i>‐C₄H₃ formation from reaction of C(³<i>P</i>_<i>j</i>) with methylacetylene, CH₃CCH (<i>X</i>¹<i>A</i>₁)
  作者：R. I. Kaiser、D. Stranges、Y. T. Lee、A. G. Suits

  DOI：10.1063/1.472677

  日期：1996.11.15

  The reaction between ground-state carbon atoms, C(3Pj), and methylacetylene, CH3CCH (X1A1), was studied at average collision energies of 20.4 and 33.2 kJ mol−1 using the crossed molecular beams technique. Product angular distributions and time-of-flight spectra of C4H3 at m/e=51 were recorded. Forward-convolution fitting of the data yields weakly polarized center-of-mass angular flux distributions isotropic at lower, but forward scattered with respect to the carbon beam at a higher collision energy. The translational energy flux distributions peak at 30–60 kJ mol−1 and show an average fractional translational energy release of 22%–30%. The maximum energy release as well as the angular distributions are consistent with the formation of the n-C4H3 radical in its electronic ground state. Reaction dynamics inferred from these distributions indicate that the carbon atom attacks the π-orbitals of the methylacetylene molecule via a loose, reactant like transition state located at the centrifugal barrier. The initially formed triplet 1-methylpropendiylidene complex rotates in a plane almost perpendicular to the total angular momentum vector around the B\C-axes and undergoes [2,3]-hydrogen migration to triplet 1-methylpropargylene. Within 1–2 ps, the complex decomposes via C–H bond cleavage to n-C4H3 and atomic hydrogen. The exit transition state is found to be tight and located at least 30–60 kJ mol−1 above the products. The explicit identification of the n-C4H3 radical under single collision conditions represents a further example of a carbon–hydrogen exchange in reactions of ground state carbon atoms with unsaturated hydrocarbons. This channel opens a versatile pathway to synthesize extremely reactive hydrocarbon radicals relevant to combustion processes as well as interstellar chemistry.