(anthracen-9-ylmethyl)triphenylphosphonium bromide | 33895-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (anthracen-9-ylmethyl)triphenylphosphonium bromide
• 英文别名: [(Anthracen-9-yl)methyl](triphenyl)phosphanium bromide；anthracen-9-ylmethyl(triphenyl)phosphanium;bromide
• CAS: 33895-18-0
• 化学式: Br*C₃₃H₂₆P
• 分子量: 533.447
• InChiKey: PKHUISHGJCJNDB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (anthracen-9-ylmethyl)triphenylphosphonium bromide 在 bis-triphenylphosphine-palladium(II) chloride sodium tetrahydroborate 、 copper(l) iodide 、 potassium tert-butylate 、 碘 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 9-(2-(4-trimethylsilylethynylphenyl)ethyl)anthracene
  参考文献：
  名称：

  Synthesis and spectroscopy of anthracene-containing linear and ‘T’-shaped π-conjugated ligands

  摘要：

  A range of new it-conjugated ethynyl- and diethynyl-benzene ligands has been synthesised and their spectroscopic characterisation carried out, most notably via IR and H-1 NMR. X-ray crystal structures were obtained for three of these ligands and one unusual ruthenium complex. Both the 4-ethynyl- and 2,5-diethynyl-benzene cores of these compounds have been functionalised through organic transformations by addition of an 9-anthracenyl. This has been attached via a range of linker moieties that vary in both their length and degree of pi-conjugation. This has given rise to two groups of compounds with either a linear, e.g., 9-(2-(4-ethynylphenyl)ethynediyl)anthracene and 9-(2-(4-ethynylphenyl)ethyl)anthracene, or 'T'-shaped morphologies, e.g., 9-(2-(2,5-diethylnylphenyl)ethyl)anthracene. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.024
• 作为产物：
  描述：

  9-蒽醇 在 吡啶 、 三溴化磷 作用下， 生成 (anthracen-9-ylmethyl)triphenylphosphonium bromide
  参考文献：
  名称：

  带有芳香族端子组的线性共轭系统。四、一些二芳基乙炔的合成

  摘要：

  1,1'-、9,9'-和1,9'-二蒽基-、2,2'-、3,3'-和9,9'-二菲基-、1,1'-的合成根据相应的 β-酮亚烷基三苯基正膦衍生物（分子内 Wittig 反应）的热解反应，描述了 2,2'-二芘基-和 6,6'-二炔基乙炔。

  DOI：

  10.1246/bcsj.44.2231

文献信息

• The synthesis of orbornadienes conjugatively linked to tetraphenylporphyrin ad anthracene: towards a norbornadiene-derived molecular electronic device
  作者：Edia E. Bonfantini、David L. Officer

  DOI：10.1039/c39940001445

  日期：——

  A facile synthesis of 2,3-disubstituted norbornadienes linked to meso-5,10,15,20-tetraphenylporphyrin ad anthracene by ethene or butadiene bridging groups is described and the potential of the derivatives to transport energy, a requirement for their action as molecular electronic devices, is discussed.

  本文描述了一种简便合成 2,3-二取代的诺尔本二烯的方法，这些诺尔本二烯通过乙烯或丁二烯桥接与美克5,10,15,20-四苯基卟啉和蒽相连，并讨论了这些衍生物在能量传输方面的潜力，这是它们作为分子电子器件作用的必要条件。
• Herstellung konjugierter Polyene mit Anthryl- und<i>N</i>-Methylpyridinium- Endgruppen
  作者：Franz Effenberger、Claus-Peter Niesert

  DOI：10.1055/s-1992-26322

  日期：——

  Preparation of Conjugated Polyenes with Anthryl and N-Methylpyridinium Terminal Groups The synthesis of terminally donor-acceptor substituted polyenes from the respective aldehydes via Horner reactions is described. As donor group the 9-anthryl and as acceptor moiety the 4-(N-methyl)pyridinium residue were chosen. A bicyclo[2.2.2]octane unit was incorporated into the chain to interrupt the conjugation. The separation and characterization of the mixtures of Z/E- isomers obtained in the syntheses was possible.

  制备具有蒽基和 N-甲基吡啶鎓末端基团的共轭多烯 描述了通过霍纳反应从相应的醛中合成末端供体-受体取代的多烯。作为供体基团，选择了 9-蒽基，作为受体分子，选择了 4-（N-甲基）吡啶残基。在链中加入了双环[2.2.2]辛烷单元以中断共轭。合成过程中获得的 Z/E- 异构体混合物的分离和表征成为可能。
• δ-Unsaturated γ-amino acids: enantiodivergent synthesis and cell imaging studies
  作者：Dnyaneshwar Kand、Dinesh Pratapsinh Chauhan、Mayurika Lahiri、Pinaki Talukdar

  DOI：10.1039/c3cc40824h

  日期：——

  Synthesis of both enantiomers of δ-unsaturated γ-amino acids via the enantiodivergent [3,3]-sigmatropic rearrangement strategy is reported. Excellent enantiomeric excess > 94% are observed in the strategy. Cell permeability of a fluorescent amino acid derivative is evaluated by live-cell imaging.

  报告通过对映异构 [3,3]-sigmatropic 重排策略合成了δ-不饱和δ-氨基酸的两种对映体。在该策略中观察到对映体过量率大于 94% 的优异对映体。通过活细胞成像评估了一种荧光氨基酸衍生物的细胞渗透性。
• Preparation of and dynamic gearing in cis-1,2-bis(9-triptycyl)ethylene
  作者：Yuzo Kawada、Hiromi Sakai、Makoto Oguri、Gen Koga

  DOI：10.1016/0040-4039(94)88184-7

  日期：1994.1

  The two tortional degrees of freedom about the bond from the bridgehead to the olefinic carbons in cis-1,2-bis(9-triptycyl)ethylene couple slightly less strongly than those in the corresponding methane in spite of the apparently deeper meshing of the two triptycyl moiety, which manifests itself in the unusually large nuclear spin-spin coupling between the olefinic protons.

  尽管两个分子之间的啮合深度明显加深，但从顺式-1，2-双（9-三甲苯基）乙烯中桥头到烯烃碳键的键的两个扭转自由度的耦合强度却比相应甲烷中的弱。三烯丙基部分，其表现为烯烃质子之间异常大的核自旋-自旋偶合。
• Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)
  作者：Henning Hopf、Christian Beck、Jean-Pierre Desvergne、Henri Bouas-Laurent、Peter G Jones、Ludger Ernst

  DOI：10.3762/bjoc.5.20

  日期：——

  The title compound, 4,13-bis[(1E,3E)-4-(9-anthracenyl)buta-1,3-dienyl][2.2]paracyclophane (2), prepared in 35% overall yield from [2.2]paracyclophane, absorbs light at lambda(max) = 400 nm with a tail down to 480 nm. By irradiation into this band, 2 generates a single photoproduct, 4, whose absorption maximum is situated at 306 nm. The starting material is recovered by irradiation at 306 nm or by heating

  标题化合物 4,13-双[(1E,3E)-4-(9-蒽基)丁-1,3-二烯基][2.2] 对环烷 (2)，由 [2.2] 对环烷以 35% 的总产率制备, 在 lambda(max) = 400 nm 处吸收光，尾部低至 480 nm。通过照射到该波段，2 生成单个光产物 4，其吸收最大值位于 306 nm。通过306nm辐射或加热回收起始材料。这种“反向”光致变色系统具有存储光学信息的潜力，化合物 4 在环境温度下在可见光下是稳定的。