2,2”-dimethoxy-1,1’:3’,1”-terphenyl | 103068-14-0

• 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: 2,2”-dimethoxy-1,1’:3’,1”-terphenyl
• 英文别名: 2,2''-dimethoxy-1,1':3',1''-terphenyl；2,2'-Dimethoxy-[1,1'3',1']Terphenyl；1,3-bis(2-methoxyphenyl)benzene
• CAS: 103068-14-0
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: QFRFJSUGFMTVSX-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  389.7±22.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2”-dimethoxy-1,1’:3’,1”-terphenyl 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 dioxacyclophane
  参考文献：
  名称：

  Oxacyclophanes based on a m-terphenyl framework

  摘要：

  m-Terphenyl tetraphenol 4 (Scheme I) and tetrabenzyl alcohol 19 (Scheme IV) were efficiently synthesized from 2,6-dichloroiodobenzene and an appropriate aryl Grignard, using tandem aryne technology. Each tetrol was used to construct bicyclic oxacyclophanes by linking the 3,3" and 5,5" substituents with bis-alkylating or acylating agents. Examples are 7, 14, 15, and 20-24. Only the meta isomer of xylylene dichloride formed a bicyclic oxacyclophane with 4; the ortho and para isomers gave polymers. However all three isomers gave oxacyclophanes (i.e., 10-12) with the diphenol 9 (only one link across the m-terphenyl framework) and bicyclic oxacyclophanes with 19 (i.e., 20-22), where each link contains two additional atoms. Para-linked 12 and 21 show restricted rotation of the p-xylylene rings. Two noninterconvertible conformers were obtained when the m-xylylene linking group contained a vicinal methoxy substituent (i.e., 15uu and 15ud).

  DOI：

  10.1021/jo00035a034
• 作为产物：
  描述：

  2,6-二溴苯胺 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 11.5h， 生成 2,2”-dimethoxy-1,1’:3’,1”-terphenyl
  参考文献：
  名称：

  A one-pot synthesis of m-terphenyls, via a two-aryne sequence

  摘要：

  DOI：

  10.1021/jo00366a016

文献信息

• Palladium-catalyzed synthesis of diarylbenzenes from coupling reactions between equal amount of diiodoarenes and arylboronic acids
  作者：Jincheng Mao、Ran Li、Yue He、Xiaojiang Yang、Dingli Wang、Yang Zhang

  DOI：10.1134/s1070427216040212

  日期：2016.4

  We reported a highly effective Pd-catalytic system for the synthesis of diarylbenzenes through Suzuki-type reaction between equal amount of diiodoarenes and arylboronic acids. This preferential oxidative addition resulted in such high selectivity.

  我们报道了通过等量二碘代芳烃和芳基硼酸之间的Suzuki型反应合成二芳基苯的高效钯催化体系。这种优先的氧化添加导致了如此高的选择性。
• Nickel-Catalyzed Monosubstitution of Polyfluoroarenes with Organozinc Reagents Using Alkoxydiphosphine Ligand
  作者：Yuki Nakamura、Naohiko Yoshikai、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ol301195x

  日期：2012.7.6

  partially fluorinated arenes. A nickel-catalyzed cross-coupling between a polyfluoroarene and an organozinc reagent in the presence of POP selectively produces a monosubstitution product. Aryl and alkylzinc reagents smoothly take part in the reaction. It is speculated that monosubstitution is the result of accelerated product expulsion from the product/catalyst complex.

  带有醇盐基团的新的二膦（POP）配体使我们能够合成部分氟化的芳烃。在POP存在下，多氟芳烃与有机锌试剂之间的镍催化交叉偶联选择性地产生单取代产物。芳基和烷基锌试剂可平稳地参与反应。据推测，单取代是产物/催化剂配合物加速排出产物的结果。
• Two Efficient Routes to m-Terphenyls from 1,3-Dichlorobenzenes
  作者：Akbar Saednya、Harold Hart

  DOI：10.1055/s-1996-4426

  日期：1996.12

  In the first route 2,6-dichlorophenyllithium (5), prepared by direct lithiation of 1,3-dichlorobenzene, reacted with aryl Grignard reagents to give m-terphenyls in 57-93% yields (Table 1); the methodology was extended to substituted 1,3-dichlorobenzenes (i.e. 8 → 10). Also, reaction of 5 with MgCl2 gave 2,6-dichlorophenylmagnesium chloride which, on warming, produced the self-capture product tetrachloro-m-terphenyl 7 in moderate yield. In the second route, reaction of 1,3-dichlorobenzene with excess of aryllithium in diethyl ether at room temperature gave the corresponding m-terphenyls in 59-94% yields (Table 2). Examples are given in which the aryllithium was prepared by three different routes (ArX+Li, ArX+t-BuLi, ArH+BuLi).

  在第一种方法中，2,6-二氯苯锂（5）是通过 1,3-二氯苯的直接石化作用制备的，它与芳基格氏试剂反应生成间三联苯，产率为 57-93%（表 1）；该方法还可扩展到取代的 1,3-二氯苯（即 8 → 10）。此外，5 与 MgCl2 反应生成 2,6-二氯苯基氯化镁，加热后生成自捕获产物四氯间三联苯 7，收率适中。在第二种方法中，1,3-二氯苯在室温下与过量的芳基锂在二乙醚中反应，得到相应的间三联苯，产率为 59-94%（表 2）。举例说明了通过三种不同途径（ArX+Li、ArX+t-BuLi、ArH+BuLi）制备芳基锂的情况。
• Synthesis of Boronate‐Based Benzo[ <i>fg</i> ]tetracene and Benzo[ <i>hi</i> ]hexacene via Demethylative Direct Borylation
  作者：Misa Numano、Naoto Nagami、Soichiro Nakatsuka、Takazumi Katayama、Kiichi Nakajima、Sou Tatsumi、Nobuhiro Yasuda、Takuji Hatakeyama

  DOI：10.1002/chem.201602753

  日期：2016.8.8

  direct borylation is reported, which was applied to the synthesis of benzo[fg]tetracenes containing boronate ester, amide, and thioester substructures. Depending on the heteroatom adjacent to boron, the molecules showed characteristic photophysical properties, molecular arrangements, and chemical stabilities. The key to the successful synthesis is the appropriate choice of the boron source and Brønsted

  报道了脱甲基的直接硼化，其被用于合成含有硼酸酯，酰胺和硫代酯亚结构的苯并[ fg ]四烷。取决于与硼相邻的杂原子，分子显示出特征性的光物理性质，分子排列和化学稳定性。到成功合成的关键是硼源和布朗斯台德碱的合适的选择。直接硼化的多功能性通过基于硼酸酯的苯并[ hi ]己二烯的合成得到证明。
• Terphenyl crowns: a new family of receptors containing ethereal canopies that direct potassium cation onto benzenoid platforms for cation–π interactions
  作者：Ruchi Shukla、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1039/b912796h

  日期：——

  We have synthesized three simple and versatile terphenyl crowns (TC) receptors containing ethereal canopies that direct a potassium cation for efficient cation–π interactions as established by 1H NMR spectroscopy and by isolation and X-ray crystallography of their K+ salts.

  通过 1H NMR 光谱以及 K+ 盐的分离和 X 射线晶体学研究，我们合成了三种简单而多用途的三联苯冠（TC）受体，它们含有能引导钾阳离子进行高效阳离子-Ï 相互作用的乙太基冠。