buta-1,3-diene-1,1,2,3,4,4-hexaylhexabenzene | 72989-40-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: buta-1,3-diene-1,1,2,3,4,4-hexaylhexabenzene
• 英文别名: 1,1,2,3,4,4-hexaphenyl-1,3-butadiene；1,1,2,3,4,4-hexaphenylbuta-1,3-diene；hexaphenyl-1,3-butadiene；1,1,2,3,4,4-hexaphenyl-buta-1,3-diene；1,1,2,3,4,4-Hexaphenyl-buta-1,3-dien；1,1,2,3,4,4-Hexaphenyl-1,3-butadien；1,1,3,4,4-pentakis-phenylbuta-1,3-dien-2-ylbenzene
• CAS: 72989-40-3
• 化学式: C₄₀H₃₀
• 分子量: 510.678
• InChiKey: GXFNMSQBHWFLIB-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C
• 沸点：
  658.8±55.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  buta-1,3-diene-1,1,2,3,4,4-hexaylhexabenzene 在 iron hydroxide oxide 、 iron(III) chloride hexahydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以88%的产率得到5,5,10,10-tetraphenyl-5,10-dihydroindeno[2,1-a]indene
  参考文献：
  名称：

  FeCl3介导的二芴基二芳基乙烷的氧化螺环化导致双螺[芴-9,5'-茚并[2,1-a]茚-10-10,9''芴] s

  摘要：

  一种新型的FeCl 3介导的氧化螺环化反应，用于构建新型的双螺链连接的π共轭分子，即双螺[芴-9,5'-茚并[2,1- a ]茚10-10,9'-芴] s（DSFIIFs），已被报道。FeCl 3与FeO（OH）的结合引发了二芴基二芳基乙烷的前所未有的双单电子​​氧化，从而以高收率提供了相应的二螺环。溶液中的最高荧光量子产率高达0.94。该方案也适用于非螺旋连接的二氢茚并茚的合成。

  DOI：

  10.1002/anie.201507794
• 作为产物：
  描述：

  在 ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到buta-1,3-diene-1,1,2,3,4,4-hexaylhexabenzene
  参考文献：
  名称：

  Three-Coordinate Iron(II) Dialkenyl Compound with NHC Ligation: Synthesis, Structure, and Reactivity

  摘要：

  The reaction of [(IPr2Me2)(2)FePh2] with PhC equivalent to CPh furnished a three-coordinate iron(II) dialkenyl complex, [(IPr2Me2)Fe(sigma-CPh=CPh2)(2)] (1, IPr2Me2 = 1,3-diisopropy1-4,5-dimethylimidazol-2-ylidene), that represents a rare example of isolable low-coordinate iron alkenyl complexes with a high-spin ground state. Complex 1 was characterized by H-1 NMR spectroscopy, solution magnetic susceptibility measurement, Mossbauer spectroscopy, single-crystal X-ray diffraction study, and elemental analyses. A reactivity study revealed the reactions of 1 with PhCh(2)C1 to produce cross-coupling product Ph2C=CPhCh(2)Ph (2), with [Cp2Fe]-[BAr4F] to yield Ph2C=CPh CPh=CPh2 (3), and with CO, 2,6-dimethylphenyl isocyanide, and phenyl azide to produce novel iron(0) and iron(II) complexes 4-6 bearing triphenylvinyl-derived ligands. These transformations demonstrated the high reactivity of the low-coordinate iron alkenyl complex.

  DOI：

  10.1021/acs.organomet.5b00632

文献信息

• Palladium/Phosphite or Phosphate Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes to Produce 1,4-Diaryl-1,3-butadienes
  作者：Hakaru Horiguchi、Hayato Tsurugi、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/adsc.200700533

  日期：2008.2.22

  The intermolecular oxidative coupling of arylboronic acids with internal alkynes efficiently proceeds in a 2:2 manner in the presence of palladium acetate, a triaryl phosphite or phosphate, and silver carbonate as catalyst, ligand, and oxidant, respectively, to produce the corresponding 1,4-diaryl-1,3-butadiene derivatives.

  芳基硼酸与内部炔烃的分子间氧化偶联可在乙酸钯，亚磷酸三芳基酯或磷酸根以及分别作为催化剂，配体和氧化剂的碳酸银存在下以2：2方式有效进行，以产生相应的1， 4-二芳基-1,3-丁二烯衍生物。
• Zirconoarylation of alkynes through <i>p</i>-chloranil-promoted reductive elimination of arylzirconates
  作者：Xiaoyu Yan、Chao Chen、Chanjuan Xi

  DOI：10.3762/bjoc.10.48

  日期：——

  A novel method for the zirconoarylation of alkynes was developed. TCQ-promoted reductive elimination of arylzirconate [LiCp₂ZrAr(RC≡CR)], which was prepared by the reaction of zirconocene–alkyne complexes with aryllithium compounds, afforded trisubstituted alkenylzirconocenes. This reaction can afford multi-substituted olefins with high stereoselectivity.

  开发了一种新颖的方法用于炔烃的锆芳基化。通过TCQ促进芳基锆酸锂化物[LiCp₂ZrAr(RC≡CR)]的还原消除，该锂化物是通过锆茂-炔基配合物与芳基锂化合物反应制备的，得到了三取代烯基锆茂。该反应可以高立体选择性地生成多取代烯烃。
• Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids
  作者：Yajing Liu、Jacky W. Y. Lam、Xiaoyan Zheng、Qian Peng、Ryan T. K. Kwok、Herman H. Y. Sung、Ian D. Williams、Ben Zhong Tang

  DOI：10.1021/acs.macromol.6b01148

  日期：2016.8.23

  PHBs showed good solubility, thermal stability, and film-forming ability. Their optical properties could be easily tuned by proper monomer design and external perturbation. The PHBs underwent active photocyclization in both solution and solid states, converting them to poly(dihydronaphthalene)s. Such a property made them promising materials for fabricating luminescent photopatterns. A new mechanistic

  原位聚合新方法在这项工作中，人们开发了由易于制备或可商购的反应物生成具有聚集诱导发射特性的发光聚合物的方法。内部炔烃和芳基硼酸的“ 1 + 2”聚偶联反应在温和的反应条件下进行，并且能够耐受水分，空气和单体化学计量失衡，从而为聚（六苯基-1,3-丁二烯）（PHB）提供了部分或部分全共轭结构，产率令人满意。所有PHB均显示出良好的溶解性，热稳定性和成膜能力。通过适当的单体设计和外部扰动，可以轻松调节其光学性能。PHB在溶液和固态下均经历了主动光环化，将其转化为聚二氢萘。这种性质使它们成为制造发光光图案的有前途的材料。提出了一种新的机制途径作为补充，以通过研究PHB的排放和相应的模型化合物来解释聚集诱导的排放（AIE）现象。
• Synthesis of Highly Substituted Symmetrical 1,3-Dienes via Organocuprate Oxidation
  作者：David Spring、Sarah. Aves、Kieron O’Connell、Kurt Pike

  DOI：10.1055/s-0031-1290116

  日期：2012.1

  Oxidation of alkenyl organocuprates formed from alkenyl halides allows the formation of highly substituted symmetrical 1,3-dienes. Cuprates formed from organolithiums and Grignard reagents can be tolerated and the reaction proceeds with retention of alkenyl geometry.

  由烯基卤化物形成的烯基有机铜酸盐发生氧化反应，可生成高度取代的对称 1,3 二烯。由有机锂和格氏试剂形成的铜酸盐也可以耐受，而且反应进行时烯基的几何形状得以保留。
• Efficient Palladium-Catalyzed Double Arylation of Phosphonoalkynes and Diarylalkynes in Water: Use of a Dinuclear Palladium(I) Catalyst
  作者：K. V. Sajna、Venu Srinivas、K. C. Kumara Swamy

  DOI：10.1002/adsc.201000579

  日期：2010.11.22

  A novel use of the dinuclear palladium(I) catalyst [(OCH2CMe2CH2O)P-S-Pd(PPh3)]2 in aqueous medium for the double arylation of phosphonoalkynes as well as diarylalkynes is reported. This double arylation requires both the iodoarene and arylboronic acid along with the catalyst. The structures of some key products have been proven by X-ray crystallography.

  报道了在水介质中双核钯（I）催化剂[（OCH 2 CMe 2 CH 2 O）PS-Pd（PPh 3）] 2在膦酰基炔烃和二芳基炔烃的双芳基化中的新用途。该双重芳基化需要碘芳烃和芳基硼酸以及催化剂。X射线晶体学已经证明了一些关键产品的结构。