1-(1,1':2',1''-三联苯-4-基)乙酮 | 5173-05-7

• 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-(1,1':2',1''-三联苯-4-基)乙酮
• 英文名称: 4-Acetyl-o-terphenyl
• 英文别名: 1-(1,1':2',1''-Terphenyl)-4-ylethan-1-one；1-[4-(2-phenylphenyl)phenyl]ethanone
• CAS: 5173-05-7
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: DVQIELBBPKJSLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  1-(1,1':2',1''-三联苯-4-基)乙酮 在 aluminum oxide 、 乙醇 、 copper oxide-chromium oxide 、 xylene 作用下， 150.0~320.0 ℃ 、7.35 MPa 条件下， 生成 4-Vinyl-o-terphenyl
  参考文献：
  名称：

  邻三联苯的化学；4-乙烯基邻三苯基。

  摘要：

  DOI：

  10.1021/jo01153a025
• 作为产物：
  描述：

  2-溴氯苯 在 palladium diacetate 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(1,1':2',1''-三联苯-4-基)乙酮
  参考文献：
  名称：

  A Practical and General Synthesis of Unsymmetrical Terphenyls

  摘要：

  [GRAPHICS]A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.

  DOI：

  10.1021/jo701308b

文献信息

• Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant
  作者：Yogesh Siddaraju、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.orglett.6b03084

  日期：2016.12.2

  A metal-free regioselective sulfenylation of the α-CH3 group of ketones has been achieved in the presence of the α-CH2 or α-CH group using the cross dehydrogenative (CDC) strategy. Aldehydes also exhibit good selectivity forming the corresponding α-sulfenylated products. This efficient sulfenylation of ketones or aldehydes with thiones or heterocyclic thiols utilizes dimethyl sulfoxide (DMSO) as an

  的α-CH的无金属区域选择性亚磺酰3组酮已在α-CH的存在下已经实现2使用交叉脱氢（CDC）的策略或α-CH基团。醛也表现出良好的选择性，形成相应的α-亚磺酰化产物。酮或醛与硫酮或杂环硫醇的这种有效的亚硫基化利用二甲基亚砜（DMSO）在碘存在下作为氧化剂。这种生态友好的方法使用了现成的廉价I 2和DMSO。通过合成Julia–Kocienski烯烃化中间体的前体已证明了该方法的应用。
• A Highly Sustainable and Active Catalyst for Suzuki-Miyaura Reaction: Palladium-Supported Ionic Liquid Catalyst (SILC) Coated with Polymer
  作者：Hisahiro Hagiwara、Kota Sato、Takashi Hoshi、Toshio Suzuki

  DOI：10.1055/s-0030-1260322

  日期：2011.10

  With the aid of an ionic liquid, palladium acetate was immobilized in the pores of silica gel, which was coated with polyethylene terephthalate. The heterogeneous catalyst was effective for Suzuki-Miyaura reactions of ortho-substituted aryl bromides, aryl triflates, and arylboronic acids in aqueous ethanol at room temperature, and could be re-used up to ten times.

  借助一种离子液体，将醋酸钯固定在涂有聚对苯二甲酸乙二醇酯的硅胶孔隙中。这种非均相催化剂对水合乙醇中室温下的邻位取代芳基溴化物、芳基三氟甲磺酸盐和芳基硼酸的铃木-宫浦反应有效，并可重复使用多达十次。
• The synthesis of some substituted biphenyl-4-carboxylic acids, 4-biphenylylacetic acids, and 4-aminobiphenyls
  作者：D. J. Byron、G. W. Gray、R. C. Wilson

  DOI：10.1039/j39660000840

  日期：——

  The synthesis of a range of substituted biphenyl-4-carboxylic acids and 4-aminobiphenyls is described. Preparations are included for the parent biphenyl-4-carboxylic acid, and for 4-biphenylylacetic acid and three substituted 4-biphenylylacetic acids.

  描述了一系列取代的联苯-4-羧酸和4-氨基联苯的合成。包括母体联苯-4-羧酸，4-联苯基乙酸和三种取代的4-联苯基乙酸的制剂。
• Immobilization of Pd on Nanosilica Dendrimer as SILC: Highly Active and Sustainable Cluster Catalyst for Suzuki-Miyaura Reaction
  作者：Hisahiro Hagiwara、Hirokazu Sasaki、Norio Tsubokawa、Takashi Hoshi、Toshio Suzuki、Tetsuya Tsuda、Susumu Kuwabata

  DOI：10.1055/s-0029-1219816

  日期：2010.8

  Palladium acetate was noncovalently immobilized as a supported ionic liquid catalyst (SILC) in a nanosilica dendrimer, PAMDMAM, with the aid of an ionic liquid to form a cluster catalyst of palladium nanoparticles. The pseudo-homogeneous hetero­genized catalyst, Pd-nanoPAMDMAM-SILC, was effective for Suzuki-Miyaura reactions of ortho-substituted aryl bromides or aryl triflates without a ligand in 50% aqueous ethanol in air at room temperature. The catalyst could be re-used up to five times in 93% average yield after simple centrifugation. TON reached 176,000.

  乙酸钯非共价地固定在纳米二氧化硅树枝状大分子PAMDMAM支持的离子液体催化剂（SILC）中，借助离子液体形成钯纳米粒子簇催化剂。这种伪均相异相化催化剂Pd-nanoPAMDMAM-SILC对室温下空气中50%乙醇水溶液中的无配体邻位取代芳基溴或芳基三氟甲磺酸酯的铃木-宫浦反应有效。催化剂经简单离心后可重复使用多达五次，平均产率为93%。TON达到176,000。
• Platinum-catalysed diborylation of arynes: synthesis and reaction of 1,2-diborylarenes
  作者：Hiroto Yoshida、Kengo Okada、Shota Kawashima、Kenji Tanino、Joji Ohshita

  DOI：10.1039/b919407j

  日期：——

  Arynes are found to be facilely inserted into bis(pinacolato)diboron by using a platinum–isocyanide catalyst, affording diverse 1,2-diborylarenes, which can be converted into o-terphenyls via Suzuki–Miyaura coupling reaction.

  研究发现，使用铂-异氰化物催化剂可以轻松将烯插入双（松香酸酯）二硼化合物中，生成多种1,2-二硼基芳烃，这些化合物可以通过铃木-宫浦偶联反应转化为邻三联苯。