(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 | 124639-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (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
• 英文别名: (1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-1,4,4a,4b,4c,5,10,10a,10b,10c-decahydro-4b,10b-dimethyl-6,9-dimethoxy-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1',2':3,4>cyclobuta<1,2-b>naphthalene；(1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,4,4a,4c,5,10,10a,10c-octahydro-1,4:5,10-dimethanobenzo<3',4'>cyclobuta<1',2':3,4>cyclobuta<1,2-b>naphthalene；(1α,4α,4aβ,4bα,4cβ,5α,10α,10aβ,10bα,10cβ)-6,9-dimethoxy-4b,10b-dimethyl-1,4,4a,4c,5,10,10a,10c-octahydro-1,4:5,10-dimethanobenzo[3',4']cyclobuta[1',2':3,4]cyclobuta[1,2-b]naphthalene；(1S,2R,3S,4S,5S,8R,9R,10R,11S,12R)-14,17-dimethoxy-3,10-dimethylheptacyclo[10.6.1.15,8.02,11.03,10.04,9.013,18]icosa-6,13,15,17-tetraene
• CAS: 124639-17-4
• 化学式: C₂₄H₂₈O₂
• 分子量: 348.485
• InChiKey: NYEOGMKFHQHLTG-DPIJRUGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (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
  参考文献：
  名称：

  一对新的刚性非对映异构三联体的合成与结构表征

  摘要：

  描述了一种用于构建完全刚性的三联体（发色团）系统D 2 -B 1 -D 1 -B 2 -A的方法，其中发色团D 2（=二甲基苯胺），D 1（= 1,4-二甲氧基萘），和A（＝二氰基ovyl）稠合到刚性烃桥B 1和B 2，其包括线性稠合的降冰片烷和双环[2.2.0]己烷单元。

  DOI：

  10.1016/0040-4020(95)00107-j

文献信息

• Synthesis, Structure, and Photophysical Studies of a Pair of Novel Rigid Bichromophoric Systems Bearing a Methyl Viologen Acceptor Unit
  作者：Donald C. Craig、Kenneth P. Ghiggino、Katrina A. Jolliffe、Steven J. Langford、Michael N. Paddon-Row

  DOI：10.1021/jo9620371

  日期：1997.4.1

  The rigid bichromophoric systems7a.2BF(4) and7b.2BF(4), comprising either a dimethoxybenzene (a) or dimethoxynaphthalene (b) unit, each covalently linked through a six-bond norbornylogous bridge to a methyl viologen unit, were synthesized with a view to studying long-range intramolecular energy (EnT) and/or electron (ET) transfer. X-ray crystallography has been used to illustrate that 7b.2BF(4) has

  刚性双发色体系7a.2BF（4）和7b.2BF（4）包含二甲氧基苯（a）或二甲氧基萘（b）单元，每个单元通过六键降冰片异源桥共价连接至甲基紫精单元，并与研究远距离分子内能量（EnT）和/或电子（ET）转移。X射线晶体学已用于说明7b.2BF（4）具有在结晶时经历自组织以在晶格内形成扩展的线性阵列的能力。对7b.2BF（4）的初步光物理研究表明，与模型二甲氧基萘单元相比，双发色团中存在一个额外的快速非辐射过程（速率常数> 2.5 x 10（10）s（-）（1））。介绍了此过程。
• Synthesis of a Variety of Bichromophoric “Ball-and-Chain” Systems Based on Buckminsterfullerene (C₆₀) for the Study of Intramolecular Electron and Energy Transfer Processes
  作者：James M. Lawson、Anna M. Oliver、Daniel F. Rothenfluh、Yi-Zhong An、George A. Ellis、Millagahamada G. Ranasinghe、Saeed I. Khan、Andreas G. Franz、Padma S. Ganapathi、Michael J. Shephard、Michael N. Paddon-Row、Yves Rubin

  DOI：10.1021/jo960512p

  日期：1996.1.1

  Diels-Alder reaction of C-60 with the 1,3-dienes 7e-h, 8a, 8b, and 8d-h affords the ''ball-and-chain'' systems 2e-h, 3a, 3b, and 3d-h bearing two chromophores linked via a rigid, hybrid saturated polynorbornane-bicyclo[2.2.0]hexane (''norbornylogous'') hydrocarbon bridge. Analogous reaction with the bis(diene) 9 affords the soluble dumbbell system 4 bearing two C-60, chromophores. The norbornylogous bridge is a strong mediator of electron and energy transfer via a through-bond coupling mechanism. The norbornylogous donor-bridge-diene units 7d-h, 8a, 8b, and 8d-h were prepared in a straightforward manner from bicyclo[2.2.2]octane precursors by extending the bridges with linearly fused norbornane-bicyclo[2.2.0]hexane moieties through execution of the tandem Mitsudo-Smith series of reactions. The X-ray structure of the dimethoxybenzene-bridge-C-60 system 3a reveals favorable self-complementarity manifested by the unusual packing structure of 3a in the crystal. Molecular mechanics, semiempirical, and ab initio conformational analyses of compounds 2e, 3a, 3b, 3e, 3f, 3h, 68, and 70 (MM2, Sybyl, CVFF, AM1, HF/3-21G) were performed to quantify their ability to adopt two nondegenerate boat conformations, i.e,, extended and folded conformers, as well as their kinetic barrier of interconversion. A similar treatment of the C-60-bridge-C-60 system 4 revealed unusual preference for the folded-folded conformer (18.9 kcal/mol at CVFF level), which was not reproduced by the AM1 method (0.11 kcal/mol). The reduction potentials of the systems 2e, 3a, and 3e were about 0.1-0.5 V more negative than C-60, and the third reduction potential (E(3)) Of the 6-bond system 2e was 0.14 V more negative than the corresponding wave for the 10-bond system 3e. This shift was attributed to the closer proximity of the dimethylaniline donor group to the C-60 surface for 2e vs 3e.
• Antolovich, Michael; Oliver, Anna M.; Paddon-Row, Michael N., Journal of the Chemical Society. Perkin transactions II, 1989, p. 783 - 790
  作者：Antolovich, Michael、Oliver, Anna M.、Paddon-Row, Michael N.

  DOI：——

  日期：——
• A study of the scope of the bismethoxycarbonylation of norbornene systems
  作者：Kate Jolliffe、Michael N Paddon-Row

  DOI：10.1016/0040-4020(94)01115-g

  日期：1995.2

  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.
• ANTOLOVICH, MICHAEL;OLIVER, ANNA M.;PADDON-ROW, MICHAEL N., J. CHEM. SOC. PERKIN TRANS. PT 2,(1989) N, C. 783-789
  作者：ANTOLOVICH, MICHAEL、OLIVER, ANNA M.、PADDON-ROW, MICHAEL N.

  DOI：——

  日期：——