1,2,5,6-tetra-exo-methylene-cyclooctane | 27567-69-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,2,5,6-tetra-exo-methylene-cyclooctane
• 英文别名: 1,2,5,6-tetra-exo-methylenecyclooctane；1,2,5,6-tetramethylenecyclooctane；1,2,5,6-Tetramethylenecyclooctan；1,2,5,6-Tetramethylencyclooctan；1,2,5,6-Tetramethylidenecyclooctane
• CAS: 27567-69-7
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: UXSIURAEVKQTGU-UHFFFAOYSA-N

物化性质

• 沸点：
  232.5±15.0 °C(Predicted)
• 密度：
  0.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,5,6-tetra-exo-methylene-cyclooctane 以23%的产率得到
  参考文献：
  名称：

  WIBERG, K. B.;OKARMA, P. J.;DAILEY, W. P., J. ORG. CHEM., 1985, 50, N 18, 3393-3395

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二溴-2,3-双(溴甲基)-2-丁烯 在 锌铜偶 作用下， 以 六甲基磷酰三胺 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1,2,5,6-tetra-exo-methylene-cyclooctane
  参考文献：
  名称：

  Preparation and selected reactions of 2,3-bis(bromomethyl)-1,3-butadiene

  摘要：

  DOI：

  10.1021/jo01293a021

文献信息

• 1,2,5,6-Tetramethylenecyclo-octane
  作者：Weston Thatcher Borden、Les Sharpe、Ieva Lazdins Reich

  DOI：10.1039/c29700000461

  日期：——

  A convenient two-step synthesis of 1,2,5,6-tetramethylenecyclo-octane from 1,2-dimethylenecyclobutane is described.

  描述了由1,2-二亚甲基环丁烷方便地两步合成1,2,5,6-四亚甲基环辛烷。
• Design and Synthesis of Extended π-Systems: Monomers, Oligomers, Polymers
  作者：U. Scherf、K. Müllen

  DOI：10.1055/s-1992-34172

  日期：——

  The synthesis of unconventional extended π-systems is described in an attempt to tailor the structures of organic compounds for specific optical and electrical properties. In order to emphasize the role of the π-conjugation and to correlate chemical structure and physical function both one-dimensional arylenevinylenes and two-dimensional ribbon-type molecules are considered. In the synthesis of the former the aryl-olefin coupling according to Heck is of special value, the synthesis of the latter is achieved by repetitive Diels-Alder cycloadditions and by two-step processes in which carefully designed polyaryl precursors are subjected to ring closure. Key ingredients of the present approach are the interplay of synthetic organic chemistry and synthetic macromolecular chemistry and the needs outlined by materials sciences. Thereby, transition from monomers to oligomers and polymers defines new requirements for the selectivity of the synthetic reactions and the tractability of the products. 1. Introduction 2. Oligo- and Poly(arylenevinylene)s 2.1. Structurally Defined Oligo(1,4-phenylenevinylene)s - Valuable Model Systems for Understanding Properties of the Corresponding Polymers 2.2. Oligomers and Polymers Containing the 9,10-Anthrylene Unit in the Main Chain 2.3. Unusual Redoxactive Systems via Incorporation of 1,5-Cyclooctatetraenylene Units 2.4. The 2,2′-Biphenylylene Building Block - toward the Generation of Photoreactive Poly(arylenevinylene)s 3. π-Systems with Ribbon- or Ladder-Type Structures 3.1. Ribbon-Type Structures via Repetitive Diels-Alder reactions 3.2. Ribbon-Type Structures via Polymer-Analogous Cyclization of Linear Precursors 3.2.1. Double-Stranded Poly(phenylene)s via Cyclization of Open-Chain Precursors 3.2.2. Oligorylenes - Synthesis of Ribbon-Type Molecules with peri-Fused Naphthalene Units 4. Conclusions

  本文介绍了非常规扩展Ï-系统的合成方法，试图调整有机化合物的结构，使其具有特定的光学和电学特性。为了强调Ï-共轭的作用，并将化学结构和物理功能联系起来，我们考虑了一维芳基乙烯和二维带状分子。在前者的合成过程中，根据 Heck 法进行的芳基-烯烃偶联具有特殊价值，而后者的合成则是通过重复的 Diels-Alder 环化反应和两步法实现的，在这两步法中，精心设计的多芳基前体要进行闭环。本方法的关键要素是合成有机化学和合成大分子化学的相互作用以及材料科学的需求。因此，从单体到低聚物和聚合物的过渡对合成反应的选择性和产品的可操作性提出了新的要求。 1. 引言 2. 低聚物和聚（芳基乙烯） 2.1. 结构明确的低聚(1,4-亚苯基乙烯)--了解相应聚合物性质的宝贵模型系统 2.2. 主链中含有 9,10-苯乙烯单元的低聚物和聚合物 2.3. 含有 1,5-环辛四烯单元的非同寻常的氧化还原体系 2.4. 2,2′-联苯基构件--走向光活性聚（芳基乙烯）的生成 3. 具有带状或梯状结构的 Ï 系统 3.1. 通过重复 Diels-Alder 反应生成的带状结构 3.2. 通过线性前体的聚合物类似环化反应生成的带状结构 3.2.1.通过开链前体环化合成双链聚亚苯基 3.2.2.低聚亚萘--具有近融合萘单元的带状分子的合成 4. 结论
• The reaction of allene with β-diketonatorhodium(I) complexes: Formation of bis(π-allylic) complexes of rhodium(III) and of rhodacyclopentane derivatives
  作者：G. Ingrosso、L. Porri、G. Pantini、P. Racanelli

  DOI：10.1016/s0022-328x(00)88776-8

  日期：1975.1

  The reaction of allene with complexes of the type (β-diketonato)Rh(C2H4)2 at temperatures between −30 and +20°, gives RhIII derivatives of formula (β-diketonato)Rh(C3H4)4, in which an allene tetramer is bonded to rhodium by two π-allylic groups. The molecular structures of these complexes were determined on the basis of the chemical behaviour, IR and NMR spectra, and, for one of them, also by X-ray

  丙二烯与（β-二酮酮）Rh（C 2 H 4）2型配合物在-30至+ 20°的温度下反应，得到式（β-二酮酮）Rh（C 3 H 4）的Rh III衍生物参照图4，其中丙二烯四聚体通过两个π-烯丙基基团键合至铑。这些配合物的分子结构是根据化学行为，IR和NMR光谱确定的，对于其中之一，还通过X射线检查确定。（Acac）Rh（C 2 H 4）2的反应在-78°下与烯丙基反应生成含有3,4-二甲基正十二环戊烷部分的新铑（III）衍生物。这些是双（π-烯丙基）络合物的前体。简要讨论了铑（III）配合物的形成机理。
• Ions derived from dianthrylethane species. How the mode of linking affects the intramolecular electron transfer
  作者：Bardo Becker、Angelika Bohnen、Marianne Ehrenfreund、Werner Wohlfarth、Yoshiteru Sakata、Walter Huber、Klaus Muellen

  DOI：10.1021/ja00004a009

  日期：1991.2

  Chemical and electrochemical reduction of dianthryl compounds affords mono-, di, tri-, and tetraanions via successive electron-transfer processes. The diamagnetic or paramagnetic ions are characterized by NMR and ESR spectroscopy, respectively, by cyclic voltammetry, and by quenching reactions. The title dianthryl systems have in common that two anthracene units are linked by ethane bridges in a sterically variable fashion. It appears that the mode of linking drastically affects the rate of intramolecular electron-transfer processes in radical monoanions as well as the charge-storage behavior.
• Transannular photochemical ring closure of 1,2,5,6-tetramethylenecyclooctane as a synthetic route to small-ring propellanes
  作者：Weston T. Borden、Ieva L. Reich、Leslie A. Sharpe、Richard B. Weinberg、Hans J. Reich

  DOI：10.1021/jo00905a005

  日期：1975.8