4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.02,6>dec-8-ene | 130552-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.02,6>dec-8-ene
• 英文别名: 4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.0^2,6>dec-8-ene；4,4-Dimethyl-3-[(2-methoxyethoxy)methoxy]tricyclo[5.2.1.0^2,6]dec-8-ene
• CAS: 130552-49-7
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: LAGDJROXKLFWQU-FQKPHLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.02,6>dec-8-ene 在 三乙基硼氢化锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 4,4-Dimethyl-3-<(2-methoxyethoxy)methoxy>tricyclo<5.2.1.0^2,6>decan-9-ol
  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：

  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