2-Brom-trans-10b,10c-dimethyl-10b,10c-dihydropyren | 71807-14-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-Brom-trans-10b,10c-dimethyl-10b,10c-dihydropyren
• CAS: 71807-14-2
• 化学式: C₁₈H₁₅Br
• 分子量: 311.221
• InChiKey: AWMPFOWMVCTZSY-IYARVYRRSA-N

物化性质

• 沸点：
  520.5±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-Brom-trans-10b,10c-dimethyl-10b,10c-dihydropyren 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  二氢芘二聚体中的高度协同光开关。

  摘要：

  我们提出了一种实现高度协作光切换的策略，其中初始切换事件极大地促进了相邻单元的后续切换。通过合适的π共轭桥连接供体/受体取代的二氢芘，与第一次开环相比，第二次光化学开环过程的量子产率可以提高两个数量级以上。结果，尽管在热回反应期间形成了中间混合开关态，但在光异构化过程中未检测到中间混合开关态。通过实验和计算比较各种二聚体的开关行为，有助于揭示连接两个光致变色单元的桥接部分的关键作用。所提出的二氢芘二聚体可作为较长协作交换链的模型系统，原则上，该系统应该能够沿着分子定义的路径高效且定向地传递信息。此外，我们的概念允许增强低聚物和聚合物系统及其材料的光敏性。

  DOI：

  10.1002/anie.202008523
• 作为产物：
  描述：

  10b,10c-dimethylpyrene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以80%的产率得到2-Brom-trans-10b,10c-dimethyl-10b,10c-dihydropyren
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008

文献信息

• A novel Birch reduction of aromatic compounds using aqueous titanium trichloride: anions of trans-10b,10c-dimethyl-2,7,10b,10c-tetrahydropyrene
  作者：Jianping Jiang、Yee-Hing Lai

  DOI：10.1016/s0040-4039(02)02785-5

  日期：2003.2

  The Birch reduction of 10b,10c-dimethyl-10b,10c-dihydropyrene 1 and anthracene could be predicted on the basis of their reduction potentials and achieved readily with aqueous titanium trichloride in near quantitative yields. Controlled reduction of a nitro group could be achieved under these conditions with the aromatic hydrocarbon remaining intact. The anion derived from the hexane obtained from reduction

  的伯奇还原10B，10C二甲基10B，10C-二氢芘的1和蒽可能他们的还原电位的基础上被预测，并用三氯化钛水溶液在接近定量的产率容易地实现。在这些条件下，可以保持芳香烃完好无损地控制硝基还原。从还原获得的己烷得到的阴离子1提供的合成路线的衍生物1从直接取代反应难以接近1。阴离子的氧化二聚导致形成了一系列有趣的产物。
• <i>N</i>-BROMOSUCCINIMIDE-CHLOROFORM, A MORE CONVENIENT METHOD TO NUCLEAR BROMINATE REACTIVE AROMATIC HYDROCARBONS
  作者：Reginald H. Mitchell、Yongsheng Chen、Ji Zhang

  DOI：10.1080/00304949709355255

  日期：1997.12
• The synthesis and trapping of the first [14]annulyne with benzyne like reactivity. A fast route to several annelated bridged annulenes.
  作者：Reginald H. Mitchell、Pengzu Zhou

  DOI：10.1016/s0040-4039(00)98049-3

  日期：1990.1
• Benzannulated annulenes. 10. Unusual macrocyclic biphenyls containing the dihydropyrene nucleus. An observation of aryl group transfer from phosphine to aryl halide using nickel complexes
  作者：Reginald H. Mitchell、Mahima Chaudhary、Thomas W. Dingle、Richard Vaughan Williams

  DOI：10.1021/ja00337a021

  日期：1984.12
• Synthesis and rotational barrier of an unsymmetrical bi-annulenyl derived from a bridged [14]annulene, a model for 1,2′-binaphthyl
  作者：Reginald H. Mitchell、Ji Zhang

  DOI：10.1016/s0040-4039(97)01518-9

  日期：1997.9

  Nickel(0) catalysed coupling of a 1:1 mixture of 2-bromo- and 4-bromo-trans-10b,10c-dimethyldihydropyrene yields 28% of the first unsymmetrically connected bi-annulenyl 4, with 33% of 2. Unlike 2, the bi-annulenyl 4 has a significant barrier to rotation which is estimated at 11.0 kcal/mole from T-c measurement compared to an MM2+PI calculated barrier of 12 kcal/mole. This is the first measurement of the barrier to rotation in a 1,2'-binaphthyl type system. (C) 1997 Elsevier Science Ltd.