1-甲基-3-(4-苯基苯基)苯 | 1459-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲基-3-(4-苯基苯基)苯
• 英文名称: 3''-methyl-[1,1';4',1'']terphenyl
• 英文别名: 3-methyl-1,1':4',1''-terphenyl；3-methylterphenyl；3-Methyl-p-terphenyl；3-Methyl-p-terphenyl；3-Methyl-terphenyl；1~3~-Methyl-1~1~,2~1~:2~4~,3~1~-terphenyl；1-methyl-3-(4-phenylphenyl)benzene
• CAS: 1459-05-8
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: LXEFZCBUUYSRCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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-甲基-3-(4-苯基苯基)苯 在 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Vinyl-p-terphenyl
  参考文献：
  名称：

  Drefahl,G.; Winnefeld,K., Journal fur praktische Chemie (Leipzig 1954), 1965, vol. 28, p. 242 - 251

  摘要：

  DOI：
• 作为产物：
  描述：

  1-([1,1'-biphenyl]-4-yl)-2-tosylethan-1-one 在 bismuth(lll) trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 硝基甲烷 、 丙酮 为溶剂， 反应 16.17h， 生成 1-甲基-3-(4-苯基苯基)苯
  参考文献：
  名称：

  Synthesis of Substituted Benzenes via Bi(OTf)₃-Mediated Intramolecular Carbonyl Allylation of α-Prenyl or α-Geranyl β-Arylketosulfones

  摘要：

  Intramolecular carbonyl allylation of alpha-prenyl or alpha-geranyl beta-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the alpha-prenylation or alpha-geranylation of 1 and the Bi(OTf)(3)-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular FriedelCrafts alkylation. A plausible mechanism has been studied and proposed.

  DOI：

  10.1021/acs.orglett.5b01461

文献信息

• Nickel- or Iron-Catalyzed Cross-Coupling of Aryl Carbamates with Arylsilanes
  作者：Wen-Juan Shi、Hong-Wei Zhao、Yang Wang、Zhi-Chao Cao、Li-Sheng Zhang、Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1002/adsc.201600590

  日期：2016.7.28

  Aryl carbamates were for the first time applied as electrophiles in the cross‐coupling with arylsilanes via nickel or iron catalysis to construct valuable biaryl compounds. This new coupling reaction features a good group tolerance and non‐sensitivity to steric hindrance on both aryl carbamates and arylsilanes.

  氨基甲酸芳基酯首次作为亲电子试剂通过镍或铁催化与芳基硅烷交叉偶联，以构建有价值的联芳基化合物。这种新的偶联反应具有良好的基团耐受性，且对氨基甲酸氨基甲酸酯和芳基硅烷均不具有空间位阻敏感性。
• A Cyclobutene-1,2-Bis(imidazolium) Salt as Efficient Precursor of Palladium-Catalyzed Room-Temperature Suzuki-Miyaura Reactions
  作者：Andreas Schmidt、Alireza Rahimi

  DOI：10.1055/s-0029-1219824

  日期：2010.6

  3,3′-[3,4-Bis(dichloromethylene)cyclobut-1-ene-1,2-diyl]bis(1-methyl-1 H-imidazolium) bis(tetrafluoroborate),palladium(II)acetate, and sodium TERT-butoxidein toluene catalyze effectively Suzuki-Miyaura cross-couplingreactions of aryl bromides, chlorides, and iodides with arylboronicacids at room temperature.

  3,3'-[3,4-双(二氯甲烷)环丁-1-烯-1,2-二基]双(1-甲基-1H-咪唑鎓)双(四氟硼酸盐)、乙酸钯(II)和钠甲苯中的叔丁醇在室温下有效地催化芳基溴化物、氯化物和碘化物与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应。
• Amide-Ligand-Controlled Highly <i>para</i>-Selective Arylation of Monosubstituted Simple Arenes with Arylboronic Acids
  作者：Yu-Xin Luan、Tao Zhang、Wei-Wei Yao、Ke Lu、Lu-Yao Kong、Yu-Tong Lin、Mengchun Ye

  DOI：10.1021/jacs.6b12907

  日期：2017.2.8

  Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.
• 273. Studies in the terphenyl series. Part III. The preparation and nitration of m-terphenyl
  作者：H. France、I. M. Heilbron、D. H. Hey

  DOI：10.1039/jr9390001288

  日期：——
• Photocatalysis of oligo(p-phenylenes): photoreductive production of hydrogen and ethanol in aqueous triethylamine
  作者：Shinjiro Matsuoka、Hiroyuki Fujii、Taisuke Yamada、Chyongjin Pac、Akito Ishida、Setsuo Takamuku、Mitsuhiro Kusaba、Nobuaki Nakashima、Shozo Yanagida

  DOI：10.1021/j100168a018

  日期：1991.7

  Oligo(p-phenylenes) (OPP-n), p-terphenyl (OPP-3) to p-sexiphenyl (OPP-6), catalyze water-reductive H2 formation and reduction of concomitantly formed acetaldehyde to ethanol upon irradiation of heterogeneous suspensions in aqueous organic solution in the presence of triethylamine (TEA) and RuCl3. Colloidal Ru0 is photoformed in situ to work as an electron relay. The activity of OPP-n increases with the number of phenylene units except for the cases of OPP-3 and of the alkylated derivatives, where the net photocatalytic activities are higher, mainly due to the effective homogeneous catalysis, since their solubilities in the solvents employed are significantly larger. The homogeneous photocatalysis of OPP-3 leads not only to H2 evolution but also to effective formation of ethanol in the absence of colloidal Ru0, being accompanied by photo-Birch reduction of OPP-3. Dynamics studies of OPP-3 reveal that photocatalysis should be initiated by formation of the excited singlet state of OPP-3 (1OPP-3*), which is reductively quenched by TEA at a rate controlled by diffusion to produce the OPP-3 radical anion (OPP-3.-) and the TEA radical cation (TEA.+). From laser flash photolysis and pulse radiolysis experiments, it is concluded that electron transfer from OPP-3.- leads to effective reduction of water to H2 catalyzed by Ru0 colloid. Furthermore, it is confirmed that OPP-3.- gives electrons directly to acetaldehyde without any electron relays like colloidal metals, resulting in the formation of ethanol. During photocatalysis, OPP-3 itself undergoes photo-Birch reduction to some extent.