(1S,2S,10R,11R,18S,19S,27R,28R)-14,15,31,32-tetrahexyl-35,36-dioxadecacyclo[26.6.1.111,18.02,27.04,25.06,23.08,21.010,19.012,17.029,34]hexatriaconta-4(25),6(23),8(21),12(17),13,15,29(34),30,32-nonaene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1S,2S,10R,11R,18S,19S,27R,28R)-14,15,31,32-tetrahexyl-35,36-dioxadecacyclo[26.6.1.111,18.02,27.04,25.06,23.08,21.010,19.012,17.029,34]hexatriaconta-4(25),6(23),8(21),12(17),13,15,29(34),30,32-nonaene
• 化学式: C₅₈H₈₀O₂
• 分子量: 809.272
• InChiKey: DEMRBDXZLHJDLQ-IJLDAJBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-dibromo-4,5-dihexylbenzene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 17.67h， 生成 (1S,2S,10R,11R,18S,19S,27R,28R)-14,15,31,32-tetrahexyl-35,36-dioxadecacyclo[26.6.1.111,18.02,27.04,25.06,23.08,21.010,19.012,17.029,34]hexatriaconta-4(25),6(23),8(21),12(17),13,15,29(34),30,32-nonaene
  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

• 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.