2,3,8,9-Tetramethylene-1,4,5,6,7,10,11,12-octahydrotetracene | 166111-55-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2,3,8,9-Tetramethylene-1,4,5,6,7,10,11,12-octahydrotetracene
• 英文别名: 2,3,8,9-Tetramethylidene-1,4,5,6,7,10,11,12-octahydrotetracene
• CAS: 166111-55-3
• 化学式: C₂₂H₂₄
• 分子量: 288.433
• InChiKey: ZFHNRUNIBYSWPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,3,8,9-Tetramethylene-1,4,5,6,7,10,11,12-octahydrotetracene 、 富马酸二乙酯 以 二氯甲烷 为溶剂， 反应 48.0h， 以66%的产率得到Tetraethyl 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16-hexadecahydrohexacene-2,3,10,11-tetracarboxylate
  参考文献：
  名称：

  Molecular ladders constituted of laterally-fused 1,4-cyclohexadiene subunits. Open-chain models of the [n]beltenes.

  摘要：

  A practical synthesis of 2,3,6,7-tetramethylene-1,4,5,8-tetrahydronaphthalene (11) has opened up several avenues for the elaboration of molecules consisting largely or exclusively of 1,2:4,5-fused 1,4-cyclohexadiene subunits. Diels-Alder addition of dienophiles to both 1,3-diene segments of this reactive hydrocarbon leads directly to 1,4,5,6,7,10,11,12-octahydrotetracene and substituted derivatives of this polyolefin. A route to the hexacene homolog is available by twofold [4 + 2] cycloaddition of a benzyne followed by Birch reduction. For reasons of solubility, the benzyne should carry alkyl groups in its 4- and 5-positions. Finally, a two-step cyclohomologation scheme is described that allows for the systematic controlled extension of the structural features present in 11 to its tetra- and hexacyclic congeners. The insolubility of the latter hydrocarbon limits its further exploitation in synthesis.

  DOI：

  10.1021/jo00123a009
• 作为产物：
  描述：

  Tetraethyl 1,4 5,8-tetrahydronaphthalene-2,3,6,7-tetracarboxylate 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三溴化磷 、 铜 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,3,8,9-Tetramethylene-1,4,5,6,7,10,11,12-octahydrotetracene
  参考文献：
  名称：

  Molecular ladders constituted of laterally-fused 1,4-cyclohexadiene subunits. Open-chain models of the [n]beltenes.

  摘要：

  A practical synthesis of 2,3,6,7-tetramethylene-1,4,5,8-tetrahydronaphthalene (11) has opened up several avenues for the elaboration of molecules consisting largely or exclusively of 1,2:4,5-fused 1,4-cyclohexadiene subunits. Diels-Alder addition of dienophiles to both 1,3-diene segments of this reactive hydrocarbon leads directly to 1,4,5,6,7,10,11,12-octahydrotetracene and substituted derivatives of this polyolefin. A route to the hexacene homolog is available by twofold [4 + 2] cycloaddition of a benzyne followed by Birch reduction. For reasons of solubility, the benzyne should carry alkyl groups in its 4- and 5-positions. Finally, a two-step cyclohomologation scheme is described that allows for the systematic controlled extension of the structural features present in 11 to its tetra- and hexacyclic congeners. The insolubility of the latter hydrocarbon limits its further exploitation in synthesis.

  DOI：

  10.1021/jo00123a009

文献信息

• Controlled Spacing of 60-Carbon Spheres with 1,4-Cyclohexadienyl Ladders by Pairwise Diels-Alder Cycloaddition to Buckminsterfullerene
  作者：Leo A. Paquette、Ron J. Graham

  DOI：10.1021/jo00115a004

  日期：1995.5
• Molecular ladders constituted of laterally-fused 1,4-cyclohexadiene subunits. Open-chain models of the [n]beltenes.
  作者：Ron J. Graham、Leo A. Paquette

  DOI：10.1021/jo00123a009

  日期：1995.9

  A practical synthesis of 2,3,6,7-tetramethylene-1,4,5,8-tetrahydronaphthalene (11) has opened up several avenues for the elaboration of molecules consisting largely or exclusively of 1,2:4,5-fused 1,4-cyclohexadiene subunits. Diels-Alder addition of dienophiles to both 1,3-diene segments of this reactive hydrocarbon leads directly to 1,4,5,6,7,10,11,12-octahydrotetracene and substituted derivatives of this polyolefin. A route to the hexacene homolog is available by twofold [4 + 2] cycloaddition of a benzyne followed by Birch reduction. For reasons of solubility, the benzyne should carry alkyl groups in its 4- and 5-positions. Finally, a two-step cyclohomologation scheme is described that allows for the systematic controlled extension of the structural features present in 11 to its tetra- and hexacyclic congeners. The insolubility of the latter hydrocarbon limits its further exploitation in synthesis.