phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone | 855288-74-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone
• 英文别名: [1,1':4',1''-terphenyl]-2'-yl(phenyl)methanone；phenyl([1,1':4',1'']terphenyl-2-yl)-methanone；phenyl([1,1';4',1'']terphenyl-2'-yl)methanone；2,5-diphenyl-benzophenone；2,5-Diphenyl-benzophenon；(2,5-Diphenylphenyl)-phenylmethanone
• CAS: 855288-74-3
• 化学式: C₂₅H₁₈O
• 分子量: 334.417
• InChiKey: NNSUABWOUMCGLN-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  554.6±39.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以40%的产率得到2-[(Z)-2-(2,5-diphenylphenyl)-1,2-diphenylethenyl]-1,4-diphenylbenzene
  参考文献：
  名称：

  High Fluorescence Efficiencies and Large Stokes Shifts of Folded Fluorophores Consisting of a Pair of Alkenyl-Tethered, π-Stacked Oligo-p-phenylenes

  摘要：

  A series of pure hydrocarbon fluorophores containing a pair of p-stacked oligo-p-phenylenes have been synthesized and analyzed by NMR and X-ray crystallography. They show good fluorescence in solutions and enhanced fluorescence in the aggregated state. Large Stokes shifts (up to 214 nm) have been achieved in these folded fluorophores in virtue of intramolecular energy transfer, and balanced structural rigidity and flexibility. These folded fluorophores provide perfect models for understanding the energy and charge transfer process in p-stacked systems.

  DOI：

  10.1021/acs.orglett.5b03152
• 作为产物：
  描述：

  2,5-二溴苯甲酸 在 aluminum (III) chloride 、 四(三苯基膦)钯 、 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 16.5h， 生成 phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone
  参考文献：
  名称：

  High Fluorescence Efficiencies and Large Stokes Shifts of Folded Fluorophores Consisting of a Pair of Alkenyl-Tethered, π-Stacked Oligo-p-phenylenes

  摘要：

  A series of pure hydrocarbon fluorophores containing a pair of p-stacked oligo-p-phenylenes have been synthesized and analyzed by NMR and X-ray crystallography. They show good fluorescence in solutions and enhanced fluorescence in the aggregated state. Large Stokes shifts (up to 214 nm) have been achieved in these folded fluorophores in virtue of intramolecular energy transfer, and balanced structural rigidity and flexibility. These folded fluorophores provide perfect models for understanding the energy and charge transfer process in p-stacked systems.

  DOI：

  10.1021/acs.orglett.5b03152

文献信息

• Lewis Acid-Catalyzed [4 + 2] Benzannulation between Enynal Units and Enols or Enol Ethers:  Novel Synthetic Tools for Polysubstituted Aromatic Compounds Including Indole and Benzofuran Derivatives
  作者：Naoki Asao、Haruo Aikawa

  DOI：10.1021/jo060597m

  日期：2006.7.1

  enynals 1, including o-(alkynyl)benzaldehydes, and carbonyl compounds 2, such as aldehydes and ketones, in the presence of a catalytic amount of AuBr3 in 1,4-dioxane at 100 °C gave the functionalized aromatic compounds 3 in high yields. Similarly, the AuBr3-catalyzed reactions of 1 with acetal compounds 5 afforded the corresponding aromatic compounds 3 in good yields. On the other hand, when the reaction

  在1,4-二恶烷中催化量的AuBr 3存在下，烯醇1（包括邻-（炔基）苯甲醛）和羰基化合物2（例如醛和酮）在100°C下反应，得到官能化的芳族化合物3高产。类似地，1与乙缩醛化合物5的AuBr 3催化反应以良好的产率提供了相应的芳族化合物3。另一方面，当反应在催化量的Cu（NTf 2）2和1当量的H 2 O在（CH 2Cl）2在100℃下，在3 ℃以上选择性地获得脱羰基萘产物4。苯并杂杂芳族化合物，例如吲哚衍生物13和苯并呋喃衍生物15，也通过使用本发明的苯环化方法合成。
• Synthesis of Acyl Terphenyls and Higher Polyaromatics via Base-Promoted C–H Functionalization of Acetylarenes with Arylacetylenes
  作者：Elena Yu. Schmidt、Elena V. Ivanova、Inna V. Tatarinova、Igor’ A. Ushakov、Nadezhda V. Semenova、Alexander V. Vashchenko、Boris A. Trofimov

  DOI：10.1021/acs.orglett.6b00782

  日期：2016.5.6

  KOtBu/DMSO-promoted C–H functionalization of acetylarenes with arylacetylenes (100 °C, 30 min), generating β,γ-ethylenic ketones, triggers upon further heating (100 °C, 4 h, with or without acidifying additive) the cascade assembly of acyl terphenyls and higher polyaromatics in good yields.

  KO t Bu / DMSO促进乙酰芳烃与芳基乙炔的C–H官能化（100°C，30分钟），生成β，γ-乙烯酮，进一步加热时触发（100°C，4 h，有或没有酸化添加剂）酰基三联苯和高级聚芳烃的级联反应，收率很高。
• Base-catalyzed cascade dimerization of γ-aryl-β,γ-enones into acylated terphenyls
  作者：Elena Yu. Schmidt、Inna V. Tatarinova、Igor A. Ushakov、Boris A. Trofimov

  DOI：10.1016/j.mencom.2016.09.003

  日期：2016.9

  4-Aryl-1-(het)arylbut-3-en-1-ones dimerize smoothly in the ButOK/DMSO superbase system at 100 °C for 4 h to afford acylated terphenyls in up to 79% yield. The dimerization is accompanied by elimination of the methylarene molecule.

  4-Butyl-1-（het）arylbut-3-en-1-ones在ButOK / DMSO超碱体系中于100°C平稳地二聚4小时，以高达79％的收率得到酰化的三联苯。二聚化伴随着甲基芳烃分子的消除。
• Palladium-catalyzed Dehydrogenative [3+3] Aromatization of Propyl Ketones and Allyl Carbonates
  作者：Kenta Koike、Satoshi Ueno

  DOI：10.1246/cl.220032

  日期：2022.4.5

  A Pd-catalyzed dehydrogenative [3+3] aromatization of 3-phenylpropyl ketones and allyl carbonates has been developed. The reaction gives various di- or tri-substituted aromatic ketones. The reaction consisting of five steps efficiently proceeded in a one-batch, one-manipulation setup. The postulated active species, η3-allyl palladium complex, works as a catalyst for triple dehydrogenations and mono

  已经开发了 3-苯丙基酮和碳酸烯丙酯的 Pd 催化脱氢 [3+3] 芳构化反应。该反应产生各种二或三取代的芳族酮。由五个步骤组成的反应在一批、一次操作的设置中有效地进行。假定的活性物质η 3 -烯丙基钯络合物可作为三重脱氢和单烯丙基化的催化剂，具有高底物控制。
• 一种1，4-二苯基-2-苯甲酰基苯的制备方法
  申请人：浙江工业大学

  公开号：CN105152896B

  公开（公告）日：2017-04-12

  本发明公开了一种式(II)所示的1，4‑二苯基‑2‑苯甲酰基苯的制备方法：将式(I)所示的(E)‑1，4‑二苯基－3－丁烯－1－酮在惰性有机溶剂中，在碱性物质作用下，在70～130℃温度下搅拌反应2～25小时，反应结束后，反应液后处理制得式(II)所示的1，4‑二苯基‑2‑苯甲酰基苯。本发明方法反应条件温和，操作方便，成本低，有着广泛的工业应用前景。