4,6-Dimethylenetricyclo<3.3.0.0^3,7>octan-2-one | 123265-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,6-Dimethylenetricyclo<3.3.0.0^3,7>octan-2-one
• 英文别名: 4,6-Dimethylentricyclo<3.3.0.0^3,7>octan-2-on；4,6-dimethylenetricyclo[3.3.0.0^3,7]octan-2-one；4,6-Dimethylidenetricyclo[3.3.0.03,7]octan-2-one；4,6-dimethylidenetricyclo[3.3.0.03,7]octan-2-one
• CAS: 123265-65-6
• 化学式: C₁₀H₁₀O
• 分子量: 146.189
• InChiKey: NIXYITMQSGFNIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  4,6-Dimethylenetricyclo<3.3.0.0^3,7>octan-2-one 以 氘代苯 为溶剂， 生成 (6aR,6bR)-4,6,6a,6b-Tetrahydro-3H-cyclopenta[cd]pentalen-1-one
  参考文献：
  名称：

  Synthesis and Properties of 2,4,6-Trimethylenetricyclo[3.3.0.03,7]octane (Stellatriene) and Its Alkyl Derivatives. Candidates for a Two-Step Cope Rearrangement

  摘要：

  The synthesis of 2,4,6-trimethylenetricyclo[3.3.0.0(3,7)] octane (stellatriene, 9), its hexamethyl derivative 37, and the spirocyclic derivatives 67 and 68, substituted at the carbon atom of the saturated bridge of the tricyclic system, are described. Key steps in the syntheses include an intramolecular Paterno-Buchi reaction leading to tetracyclic oxetanes (e.g., 22b, 39, 47, 59, and 60) as well as the cleavage of the oxetane ring induced by various bases. During the synthesis several dienones were prepared (35, 41, 50, 63, and 64). The trienes and the dienones rearrange to triquinane derivatives at temperatures between 25 and 50 degrees C. The half-lives of the molecules in solution have been determined, which indicate only a moderate effect of the methyl groups on the stability. The rearranged products can best be explained by assuming a stepwise Cope rearrangement via two allylic fragments.

  DOI：

  10.1021/jo00084a019
• 作为产物：
  描述：

  endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene 在 chromium trioxide-pyridine complex 、 dipyridine chromium trioxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 4,6-Dimethylenetricyclo<3.3.0.0^3,7>octan-2-one
  参考文献：
  名称：

  Gleiter, Rolf; Sigwart, Christoph; Kissler, Bernd, Angewandte Chemie, 1989, vol. 101, # 11, p. 1561 - 1563

  摘要：

  DOI：

文献信息

• Gleiter, Rolf; Sigwart, Christoph; Kissler, Bernd, Angewandte Chemie, 1989, vol. 101, # 11, p. 1561 - 1563
  作者：Gleiter, Rolf、Sigwart, Christoph、Kissler, Bernd

  DOI：——

  日期：——
• Lange, Holger; Loeb, Patrick; Herb, Thilo, journal of the chemical society-perkin transactions 2, 2000, # 6, p. 1155 - 1163
  作者：Lange, Holger、Loeb, Patrick、Herb, Thilo、Gleiter, Rolf

  DOI：——

  日期：——
• Synthesis and Properties of 2,4,6-Trimethylenetricyclo[3.3.0.03,7]octane (Stellatriene) and Its Alkyl Derivatives. Candidates for a Two-Step Cope Rearrangement
  作者：Rolf Gleiter、Christoph Sigwart

  DOI：10.1021/jo00084a019

  日期：1994.3

  The synthesis of 2,4,6-trimethylenetricyclo[3.3.0.0(3,7)] octane (stellatriene, 9), its hexamethyl derivative 37, and the spirocyclic derivatives 67 and 68, substituted at the carbon atom of the saturated bridge of the tricyclic system, are described. Key steps in the syntheses include an intramolecular Paterno-Buchi reaction leading to tetracyclic oxetanes (e.g., 22b, 39, 47, 59, and 60) as well as the cleavage of the oxetane ring induced by various bases. During the synthesis several dienones were prepared (35, 41, 50, 63, and 64). The trienes and the dienones rearrange to triquinane derivatives at temperatures between 25 and 50 degrees C. The half-lives of the molecules in solution have been determined, which indicate only a moderate effect of the methyl groups on the stability. The rearranged products can best be explained by assuming a stepwise Cope rearrangement via two allylic fragments.