| 107426-40-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• CAS: 107426-40-4
• 化学式: C₁₈H₂₂
• 分子量: 238.373
• InChiKey: GOLIPWRXIQMYRT-YUDBWQHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  四溴对烯 、 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以79%的产率得到DN-6
  参考文献：
  名称：

  An Efficient Synthetic Strategy for Naphthalene Annellation of Norbornenylogous Systems

  摘要：

  由 4 和碘化钠生成的二溴萘醌（5）被亲二烯的降冰片基底物原位捕获，可以很容易地实现降冰片基化合物的萘环化，而且产量很高。 使用过的亲二烯烃包括降冰片二烯（根据不同的条件，可得到单加合物 8b 或双加合物 3a）、降冰片烯、苯并降冰片二烯 (11)、二烯 9 和 13。

  DOI：

  10.1055/s-1986-31603
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以85%的产率得到
  参考文献：
  名称：

  新的线性和角度系统的合成，可用作分子设计中的刚性棒和间隔子

  摘要：

  对各种取代的降冰片烯进行金属催化的[2 + 2]环加成反应，生成活化的环丁烯，该环丁烯与四环烷进一步反应生成直链双二烯，或与环戊二烯形成角双二烯；这些联二烯是刚性的脂环族骨架，可供合成化学家用于分子设计。

  DOI：

  10.1039/c39830001340

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.