(1R,2S,3R,4R,5R,6S,7S,10R,11R,12S,13S,14S,15R,16S)-25,25-dimethoxy-3,14-dimethylnonacyclo[14.6.1.15,12.17,10.02,15.03,14.04,13.06,11.017,22]pentacosa-8,17,19,21-tetraene | 180396-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S,3R,4R,5R,6S,7S,10R,11R,12S,13S,14S,15R,16S)-25,25-dimethoxy-3,14-dimethylnonacyclo[14.6.1.15,12.17,10.02,15.03,14.04,13.06,11.017,22]pentacosa-8,17,19,21-tetraene
• CAS: 180396-68-3
• 化学式: C₂₉H₃₄O₂
• 分子量: 414.588
• InChiKey: AQQULNMLFOAQBR-XGFHMVPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R,5R,6S,7S,10R,11R,12S,13S,14S,15R,16S)-25,25-dimethoxy-3,14-dimethylnonacyclo[14.6.1.15,12.17,10.02,15.03,14.04,13.06,11.017,22]pentacosa-8,17,19,21-tetraene 在 甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (1R,2S,3R,4R,5R,6S,7S,10R,11R,12S,13S,14S,15R,16S)-3,14-dimethylnonacyclo[14.6.1.15,12.17,10.02,15.03,14.04,13.06,11.017,22]pentacosa-8,17,19,21-tetraen-25-one
  参考文献：
  名称：

  A synthetic strategy for the construction of a novel series of rigid supramolecular triads

  摘要：

  描述了一种构建完全刚性的三元超分子系统的方法，该系统为D2–B1–D1–B2–A，其中的色谱体D2(二甲基苯胺)、D1(二甲氧基萘)和A(二氰乙烯)与由线性融合的诺博烯和自行车[2.2.0]己烷单元组成的桥接体B1和B2相结合。

  DOI：

  10.1039/c39930001641
• 作为产物：
  描述：

  5,5-二甲氧基-1,2,3,4-四氯环戊二烯 在 sodium 、 异丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 生成 (1R,2S,3R,4R,5R,6S,7S,10R,11R,12S,13S,14S,15R,16S)-25,25-dimethoxy-3,14-dimethylnonacyclo[14.6.1.15,12.17,10.02,15.03,14.04,13.06,11.017,22]pentacosa-8,17,19,21-tetraene
  参考文献：
  名称：

  A synthetic strategy for the construction of a novel series of rigid supramolecular triads

  摘要：

  描述了一种构建完全刚性的三元超分子系统的方法，该系统为D2–B1–D1–B2–A，其中的色谱体D2(二甲基苯胺)、D1(二甲氧基萘)和A(二氰乙烯)与由线性融合的诺博烯和自行车[2.2.0]己烷单元组成的桥接体B1和B2相结合。

  DOI：

  10.1039/c39930001641

文献信息

• 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.
• A synthetic strategy for the construction of a novel series of rigid supramolecular triads
  作者：James M. Lawson、Michael N. Paddon-Row

  DOI：10.1039/c39930001641

  日期：——

  A method is described for constructing totally rigid triad(trichromophoric) supramolecular systems, D2–B1–D1–B2–A, in which the chromophores D2(dimethylaniline), D1(dimethoxynaphthalene), and A(dicyanovinyl) are fused to bridges, B1 and B2, consisting of linearly fused norbornyl and bicycle[2.2.0]hexanyl units.

  描述了一种构建完全刚性的三元超分子系统的方法，该系统为D2–B1–D1–B2–A，其中的色谱体D2(二甲基苯胺)、D1(二甲氧基萘)和A(二氰乙烯)与由线性融合的诺博烯和自行车[2.2.0]己烷单元组成的桥接体B1和B2相结合。