Tetraethyl 1,4,5,6,7,10,11,12-octahydrotetracene-2,3,8,9-tetracarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Tetraethyl 1,4,5,6,7,10,11,12-octahydrotetracene-2,3,8,9-tetracarboxylate
• 化学式: C₃₀H₃₆O₈
• 分子量: 524.611
• InChiKey: XLRVMIOKCDNJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3,6,7-Tetramethylene-1,4,5,8-tetrahydronaphthalene 、 丁炔二酸二乙酯 以 乙醚 为溶剂， 反应 72.0h， 以40%的产率得到Tetraethyl 1,4,5,6,7,10,11,12-octahydrotetracene-2,3,8,9-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