dimethyl (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4c,5,10,10a,10c-decahydro-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1,2-b>-napthalene-2-exo,3-exo-dicarboxylate | 168103-33-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: dimethyl (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4c,5,10,10a,10c-decahydro-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1,2-b>-napthalene-2-exo,3-exo-dicarboxylate
• CAS: 168103-33-1
• 化学式: C₂₈H₃₄O₆
• 分子量: 466.574
• InChiKey: COAFZKJDZZVOQM-PYFIUJTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  dimethyl (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4c,5,10,10a,10c-decahydro-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1,2-b>-napthalene-2-exo,3-exo-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  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：

  甲醇 、 一氧化碳 、 (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 sodium acetate 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以80%的产率得到dimethyl (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,2,3,4,4a,4c,5,10,10a,10c-decahydro-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1,2-b>-napthalene-2-exo,3-exo-dicarboxylate
  参考文献：
  名称：

  A study of the scope of the bismethoxycarbonylation of norbornene systems

  摘要：

  Stille-Vogel bismethoxycarbonylation of a series of norbornene-type monoenes, 9-15, and nonconjugated dienes, 16 and 17 was studied. Three significant findings ate: (1) Bismethoxycarbonylation reactions may be carried out using CO at atmospheric pressure. (2) The sensitive p-methoxybenzyl protecting group withstands the Stille-Vogel reaction conditions. (3) The bismethoxycarbonylation reaction may be carried out using THF as a cosolvent, although reaction times are longer.

  DOI：

  10.1016/0040-4020(94)01115-g