1,3-Dicyclopropyl-propanon-(1) | 14113-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dicyclopropyl-propanon-(1)
• 英文别名: 1,3-Dicyclopropyl-1-propanone；1,3-dicyclopropylpropan-1-one
• CAS: 14113-97-4
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: JVEKMDALAXMAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 双环丙基酮 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 生成 1,3-Dicyclopropyl-propanon-(1)
  参考文献：
  名称：

  Hanack,M.; Ensslin,H.M., Justus Liebigs Annalen der Chemie, 1966, vol. 697, p. 100 - 110

  摘要：

  DOI：

文献信息

• Bridged spiropentanes: Ring expansion
  作者：Kenneth B. Wiberg、John R. Snoonian

  DOI：10.1016/0040-4039(94)02489-x

  日期：1995.2

  Diazomethane ring expansion of tricyclo[4.1.0.01,3]heptan-4-one provides a convenient route to three carbon-bridged spiropentanes. The relative rates of reaction and the migratory preferences of cyclopropyl vs methylene were examined for several cyclopropyl alkyl ketones, and were correlated with the results of HF/6-31G∗ MO calculations.

  三环[4.1.0.0 1,3 ]庚烷-4-酮的重氮甲烷环扩环提供了通往三个碳桥联螺环戊烷的便捷途径。研究了几种环丙基烷基酮的相对反应速率以及环丙基与亚甲基的迁移偏好，并将其与HF / 6-31G * MO计算结果相关联。
• Ring Expansion and Contraction of a Two-Carbon Bridged Spiropentane
  作者：Kenneth B. Wiberg、John R. Snoonian

  DOI：10.1021/jo970980e

  日期：1998.3.1

  The reactions of tricyclo[4.1.0.0(1,3)]heptan-4-one (5) and two related systems with diazomethane and m-CPBA were examined in order to determine the relative reactivity and migratory aptitudes for the three compounds. The reactions of 5 with diazomethane and m-CPBA yielded new derivatives of the tricyclo[5.1.0.0(1,3)]octane ring system that showed that migration of cyclopropylcarbinyl is favored over cyclopropyl migration in this system. Photolysis of 5-diazotricyclo[4.1.0.0(1,3)]heptan-4-one (23) in methanol and dimethylamine did not lead to ring contraction to the tricyclo[3.1.0.0(1,3)]hexane ring system, but an interesting product was derived from an unusual rearrangement process in the photolysis in dimethylamine. Matrix photolysis of 23 at 15 K gave a decrease in the diazo band at 2085 cm(-1) and the appearance of a new band at 2117 cm(-1), which is a normal position expected for a small-ring ketene such as cyclopropylketene. Thus, matrix photolysis appears to have yielded a derivative of the previously unknown tricyclo[3.1.0.0(1,3)]hexane ring system. The lithium enolate of 5 was characterized by NMR spectroscopy at -80 degrees C and was found to rearrange to m-cresol at -65 degrees C. The geometries of the bridged spiropentanes of this work were optimized at the MP2(frozen core)/6-31G* level of theory, and group equivalent values were derived in order to calculate the heats of formation for these compounds using the calculated energies.
• Hanack,M.; Ensslin,H.M., Justus Liebigs Annalen der Chemie, 1966, vol. 697, p. 100 - 110
  作者：Hanack,M.、Ensslin,H.M.

  DOI：——

  日期：——