3,4-dimethylbicyclo<4.3.0>nona-3,8-dien-7-one | 136339-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dimethylbicyclo<4.3.0>nona-3,8-dien-7-one
• 英文别名: 5,6-dimethyl-3a,4,7,7a-tetrahydroinden-1-one
• CAS: 136339-03-2
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: ATDAWVPQNAWHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-acetoxy-cyclopentenone 、 2,3-二甲基-1,3-丁二烯 在 zinc(II) chloride 氢氧化钾 作用下， 生成 3,4-dimethylbicyclo<4.3.0>nona-3,8-dien-7-one
  参考文献：
  名称：

  4-Acetoxycyclopent-2-enone: a synthetic equivalent for cyclopentadienone in diels-alder reactions

  摘要：

  The Lewis acid catalyzed Diels-Alder reactions of 4-acetoxycyclopentenone 5 with both cyclic and acyclic dienes is described. Subsequent base induced elimination of the beta-acetoxy group from the respective cycloadducts leads to bi- and tricyclic enones in good yields. The pi-facial diastereoselectivity of the cycloaddition of 5 with cyclopentadiene is 3:1, in favor of the anti-adduct 6a.

  DOI：

  10.1016/s0040-4039(00)79782-6

文献信息

• 4-hydroxycyclopent-2-en-1-one and derivatives as chiral synthetic equivalents of cyclopentadienone in asymmetric diels-alder reactions
  作者：Paul P M.A. Dols、Antonius J.H. Klunder、Binne Zwanenburg

  DOI：10.1016/s0040-4020(01)85571-x

  日期：1994.1
• Dols Paul P. M. A., Klunder Antonius J. H., Zwanenburg Binne, Tetrahedron, 50 (1994) N 28, S 8515-8538
  作者：Dols Paul P. M. A., Klunder Antonius J. H., Zwanenburg Binne

  DOI：——

  日期：——
• 4-Acetoxycyclopent-2-enone: a synthetic equivalent for cyclopentadienone in diels-alder reactions
  作者：P.P.M.A. Dols、L. Lacroix、A.J.H. Klunder、B. Zwanenburg

  DOI：10.1016/s0040-4039(00)79782-6

  日期：1991.7

  The Lewis acid catalyzed Diels-Alder reactions of 4-acetoxycyclopentenone 5 with both cyclic and acyclic dienes is described. Subsequent base induced elimination of the beta-acetoxy group from the respective cycloadducts leads to bi- and tricyclic enones in good yields. The pi-facial diastereoselectivity of the cycloaddition of 5 with cyclopentadiene is 3:1, in favor of the anti-adduct 6a.