3-Methyl-3-(2-methyl-2-propenyl)cyclopentanon | 64631-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-3-(2-methyl-2-propenyl)cyclopentanon
• 英文别名: 3-Methyl-3-(2-methylprop-2-enyl)cyclopentan-1-one；3-methyl-3-(2-methylprop-2-enyl)cyclopentan-1-one
• CAS: 64631-70-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: HOCDTUMNMQHROC-UHFFFAOYSA-N

物化性质

• 沸点：
  207.1±9.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-Methyl-3-(2-methyl-2-propenyl)cyclopentanon 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 3-Isobutyl-3-methylcyclopentanon
  参考文献：
  名称：

  Photochemistry of 4-isobutyl-4-methyl- and 4-(2-methoxyethyl)-4-methyl-2-cyclopentenone. Stereochemical effects in intramolecular abstraction of hydrogen by the .beta.-carbon atom of cyclopentenones

  摘要：

  DOI：

  10.1021/ja00460a024
• 作为产物：
  描述：

  4-Methyl-4-isobutylcyclopentenon 以 苯 为溶剂， 生成 3-Methyl-3-(2-methyl-2-propenyl)cyclopentanon
  参考文献：
  名称：

  Photochemistry of 4-isobutyl-4-methyl- and 4-(2-methoxyethyl)-4-methyl-2-cyclopentenone. Stereochemical effects in intramolecular abstraction of hydrogen by the .beta.-carbon atom of cyclopentenones

  摘要：

  DOI：

  10.1021/ja00460a024

文献信息

• Determination of the Relative Rates of Formation, Fates, and Structures of Triplet 1,4-Biradicals Generated in the Photochemical Cycloaddition Reactions of 2-Cyclopentenones with 2-Methylpropene
  作者：David Andrew、Alan C. Weedon

  DOI：10.1021/ja00126a005

  日期：1995.5

  The structures and relative rates of formation of the isomeric triplet 1,4-biradical intermediates generated in the photocycloaddition reactions between 2-methylpropene and each of 2-cyclopentenone, 2-methyl-2-cyclopentenone, and 3-methyl-2-cyclopentenone were determined. This was accomplished by using hydrogen selenide as a hydrogen atom donor to trap quantitatively the 1,4-biradicals formed in each reaction, The quantum yields of cycloadduct formation in the photocycloaddition reactions were measured as a function of alkene concentration. For each reaction the relative rates of formation of the biradicals and the quantum yield data were combined to determine quantitatively how each biradical partitions between closure (or disproportionation) to product and fragmentation to ground state enone and alkene. It is concluded that the regiochemistry of the enone-alkene photocycloaddition reactions studied is dominated by the manner in which the biradical intermediates partition between products and ground state precursors and not by the relative rates at which they are formed. It is also concluded that methyl substitution at the 3-position of cyclopentenone has little effect on either the relative rates of formation of the various isomeric biradical intermediates or the manner in which they partition between products and starting materials. However, methyl substitution at the 2-position of cyclopentenone slows formation of biradicals in which the alkene is bonded to the enone 2-position and also inhibits closure to cyclobutane products of biradicals formed by bonding of the alkene to the 3-position of the enone. These results can be rationalized if it is assumed that the enone triplet excited state possesses a planar carbon at the 2-position and a pyramidalized carbon at the 3-position, and if it is also assumed that in the biradicals, radical centers at the cyclopentanone 2-position are planar and at the 3-position are pyramidalized.
• Photochemistry of 4-isobutyl-4-methyl- and 4-(2-methoxyethyl)-4-methyl-2-cyclopentenone. Stereochemical effects in intramolecular abstraction of hydrogen by the .beta.-carbon atom of cyclopentenones
  作者：Semiramis Ayral-Kaloustian、Steven Wolff、William C. Agosta

  DOI：10.1021/ja00460a024

  日期：1977.8