((1R,2R,3S,4S,4aR,4bR,4cS,5R,10S,10aR,10bS,10cS)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4b,4c,5,10,10a,10b,10c-dodecahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene-2,3-diyl)bis(methylene) diacetate | 220957-14-2

• 分子结构分类: 有机化合物
• 英文名称: ((1R,2R,3S,4S,4aR,4bR,4cS,5R,10S,10aR,10bS,10cS)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4b,4c,5,10,10a,10b,10c-dodecahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene-2,3-diyl)bis(methylene) diacetate
• CAS: 220957-14-2
• 化学式: C₃₀H₃₈O₆
• 分子量: 494.628
• InChiKey: WBLGKAAOGGKPFO-ONXBVCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((1R,2R,3S,4S,4aR,4bR,4cS,5R,10S,10aR,10bS,10cS)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4b,4c,5,10,10a,10b,10c-dodecahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene-2,3-diyl)bis(methylene) diacetate 在 silver(II) oxide 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以91%的产率得到((1R,2R,3S,4S,4aR,4bR,4cS,5R,10S,10aR,10bS,10cS)-4b,10b-dimethyl-6,9-dioxo-1,2,3,4,4a,4b,4c,5,6,9,10,10a,10b,10c-tetradecahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene-2,3-diyl)bis(methylene) diacetate
  参考文献：
  名称：

  Design and Synthesis of Two (Pseudo)symmetric Giant Trichromophoric Systems Containing the C₆₀ Chromophore

  摘要：

  Diels-Alder reaction of C-60 with the 1,3-dienes syn-5 and syn-20 affords the giant trichromophoric systems syn-C-60-5-DMN-6-P-Zn and syn-C-60-9-DMN-6-DMA, respectively, in which the three chromphores in each system are Linked via rigid, hybrid saturated polynorbornane-bicyclo[2.2.0]-hexane ("norbornylogous") hydrocarbon bridges. The norbornylogous bridge is a strong mediator of electron and energy transfer via a through-bond coupling mechanism. Hence, the giant trichromophores described herein illustrate the necessary methodology for the synthesis of efficient molecular systems that are capable of generating long-lived charge-separated states. The 1,3-dienes syn-5 and syn-20 were prepared in a straightforward manner from two fragments containing a diene and a dienophile, and thus a simple building-block approach to such sophisticated systems is described. Semiempirical AM1 MO SCF calculations were carried out on the trichromophoric systems to quantify their ability to adopt two nondegenerate boat conformations, i.e., extended and folded conformers.

  DOI：

  10.1021/jo981940t
• 作为产物：
  描述：

  (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-1,4,4a,4b,4c,5,10,10a,10b,10c-decahydro-1,4:5,10-dimethano-6,9-dimethoxy-4b,10b-dimethylbenzo<3',4'>cyclobuta<1',2':3,4>cyclobuta<1,2-b>naphthalene 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium acetate 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 ((1R,2R,3S,4S,4aR,4bR,4cS,5R,10S,10aR,10bS,10cS)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4b,4c,5,10,10a,10b,10c-dodecahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene-2,3-diyl)bis(methylene) diacetate
  参考文献：
  名称：

  Design and Synthesis of Two (Pseudo)symmetric Giant Trichromophoric Systems Containing the C₆₀ Chromophore

  摘要：

  Diels-Alder reaction of C-60 with the 1,3-dienes syn-5 and syn-20 affords the giant trichromophoric systems syn-C-60-5-DMN-6-P-Zn and syn-C-60-9-DMN-6-DMA, respectively, in which the three chromphores in each system are Linked via rigid, hybrid saturated polynorbornane-bicyclo[2.2.0]-hexane ("norbornylogous") hydrocarbon bridges. The norbornylogous bridge is a strong mediator of electron and energy transfer via a through-bond coupling mechanism. Hence, the giant trichromophores described herein illustrate the necessary methodology for the synthesis of efficient molecular systems that are capable of generating long-lived charge-separated states. The 1,3-dienes syn-5 and syn-20 were prepared in a straightforward manner from two fragments containing a diene and a dienophile, and thus a simple building-block approach to such sophisticated systems is described. Semiempirical AM1 MO SCF calculations were carried out on the trichromophoric systems to quantify their ability to adopt two nondegenerate boat conformations, i.e., extended and folded conformers.

  DOI：

  10.1021/jo981940t