4-Methyltricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one | 85806-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Methyltricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one
• 英文别名: (1R,2R,6R,7S)-4-methyltricyclo[5.2.1.02,6]deca-4,8-dien-3-one
• CAS: 85806-42-4
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: QVHOHWFDWAKDCD-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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-Methyltricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one 在 甲醇 、 lithium aluminium tetrahydride 、 氨 、 lithium 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.02,6>dec-8-ene
  参考文献：
  名称：

  Stereocontrolled synthesis of functionalized diquinanes from Pauson-Khand-derived exo-tricyclo[5.2.1.02,6]decenones

  摘要：

  A 10-step sequence is described for the conversion of 4-methyl-exo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one (the Pauson-Khand cycloaddition product of norbornadiene with propyne) into 3,3-dimethyl-2-[(2-methoxyethoxy)methoxy]-8-(1-methyl-2-oxopropyl)bicyclo[3.3.0]octan-6-ol. The latter diquinane, formed with complete stereocontrol and well-differentiated functionality, is appropriately substituted to serve as an entry to highly functionalized linearly fused triquinanes, although attempts to close a third five-membered ring via an enolate-epoxide ring-opening process were unsuccessful.

  DOI：

  10.1021/jo00001a063
• 作为产物：
  描述：

  2-ethyl-2,5-dimethoxy-2,5-dihydro-furan 在 硫酸 、 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 生成 4-Methyltricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one
  参考文献：
  名称：

  闪蒸真空热取代取代的三环[5.2.1.0 2,6 ]癸烯的立体特异性全合成（±）戊霉素

  摘要：

  描述了从呋喃开始合成4-官能化的三环[5.2.1.0 2,6 ]癸烯。这些结构被证明是用于合成环戊烯类化合物如戊霉素和类似物的合适的前体。

  DOI：

  10.1016/0040-4039(82)80158-5

文献信息

• Stereospecific total synthesis of (±) pentenomycins by flash vacuum thermolysis of substituted tricyclo[5.2.1.02,6]decenones
  作者：J.M.J. Verlaak、A.J.H. Klunder、B. Zwanenburg

  DOI：10.1016/0040-4039(82)80158-5

  日期：1982.1

  The synthesis of 4-functionalized tricyclo[5.2.1.02,6]decenones , starting from furans, is described. These structures are shown to be suitable precursors for the synthesis of cyclopentenoids such as pentenomycin and analogs.

  描述了从呋喃开始合成4-官能化的三环[5.2.1.0 2,6 ]癸烯。这些结构被证明是用于合成环戊烯类化合物如戊霉素和类似物的合适的前体。
• Stereocontrolled synthesis of functionalized diquinanes from Pauson-Khand-derived exo-tricyclo[5.2.1.02,6]decenones
  作者：Susan E. MacWhorter、Neil E. Schore

  DOI：10.1021/jo00001a063

  日期：1991.1

  A 10-step sequence is described for the conversion of 4-methyl-exo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one (the Pauson-Khand cycloaddition product of norbornadiene with propyne) into 3,3-dimethyl-2-[(2-methoxyethoxy)methoxy]-8-(1-methyl-2-oxopropyl)bicyclo[3.3.0]octan-6-ol. The latter diquinane, formed with complete stereocontrol and well-differentiated functionality, is appropriately substituted to serve as an entry to highly functionalized linearly fused triquinanes, although attempts to close a third five-membered ring via an enolate-epoxide ring-opening process were unsuccessful.