5-methyl-1,1'-biphenyl-2-carbonitrile | 42308-22-5

• 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: 5-methyl-1,1'-biphenyl-2-carbonitrile
• 英文别名: 5-Methyl[1,1'-biphenyl]-2-carbonitrile；4-methyl-2-phenylbenzonitrile
• CAS: 42308-22-5
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: LCNOLIKTKXWFMV-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  362.2±21.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-1,1'-biphenyl-2-carbonitrile 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 生成 6β-(5-methyl-biphenyl-2-carbonylamino)-penicillanic acid
  参考文献：
  名称：

  半合成青霉素。I.2-联苯苄青霉素。

  摘要：

  DOI：

  10.1021/jm00333a001
• 作为产物：
  描述：

  苯硼酸 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver fluoride 、 特戊酸钠 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 5.0h， 生成 5-methyl-1,1'-biphenyl-2-carbonitrile
  参考文献：
  名称：

  Controllable Rh(III)-Catalyzed C–H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates

  摘要：

  A controllable Rh(III)-catalyzed C-H arylation and dealcoholization of benzimidates with arylboronic esters was developed, delivering various biphenyl-2-carbonitriles and biphenyl-2-carbimidates by simply tuning the reaction conditions. This approach features high efficiency, good functional group tolerance, and easy operation. It also provides an alternative pathway to thoroughly exploit the directing group in transition-metal-catalyzed C-H activations.

  DOI：

  10.1021/acs.orglett.8b02915

文献信息

• ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND DIAGNOSTIC COMPOSITION INCLUDING THE ORGANOMETALLIC COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20200392173A1

  公开（公告）日：2020-12-17

  Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound. M 1 (L 11 ) n11 (L 12 ) n12 L 11 in Formula 1 is a ligand represented by Formula 1-1, and other substituents are the same as described in the detailed description of the specification:

  提供的是由化学式1表示的有机金属化合物，包括该有机金属化合物的有机发光器件，以及包括该有机金属化合物的诊断组合物。 M 1 (L 11 ) n11 (L 12 ) n12 <化学式1> 化学式1中的L 11 是由化学式1-1表示的配体，其他取代基与规范的详细描述中描述的相同。
• Rational Development of Remote C−H Functionalization of Biphenyl: Experimental and Computational Studies
  作者：Zhoulong Fan、Katherine L. Bay、Xiangyang Chen、Zhe Zhuang、Han Seul Park、Kap‐Sun Yeung、K. N. Houk、Jin‐Quan Yu

  DOI：10.1002/anie.201915624

  日期：2020.3.16

  compounds is reported. Compared to the previous approach of installing a complex U-shaped template to achieve a molecular U-turn and assemble the large-sized cyclophane transition state for the remote C-H activation, a synthetically useful phenyl nitrile functional group could also direct remote meta-C-H activation. This reaction provides a useful method for the modification of biaryl compounds because

  报道了一种简单而有效的腈引导的间-CH烯化、乙酰氧基化和联芳基化合物的碘化。与之前安装复杂的U型模板以实现分子掉头并组装大尺寸环芳过渡态以进行远程CH活化的方法相比，合成有用的苯基腈官能团也可以直接远程间位CH活化。该反应为联芳基化合物的改性提供了一种有用的方法，因为腈基可以很容易地转化为胺、酸、酰胺或其他杂环。值得注意的是，从之前使用大环芳腈模板的结果中无法预期联苯腈的远程间位选择性。DFT 计算研究表明，含有配体的 Pd-Ag 异二聚过渡态 (TS) 有利于所需的远程元选择性。对照实验证明了腈基团的定向作用并排除了非定向元-CH激活的可能性。研究发现，取代的 2-吡啶酮配体在协同金属化-去质子化 (CMD) 过程中协助间位 CH 键断裂的关键。
• [IL]2[PdCl4] complexes (IL=imidazolium cation) as efficient catalysts for Suzuki–Miyaura cross-coupling of aryl bromides and aryl chlorides
  作者：E. Silarska、A.M. Trzeciak、J. Pernak、A. Skrzypczak

  DOI：10.1016/j.apcata.2013.06.046

  日期：2013.9

  were also obtained in the Suzuki–Miyaura reaction of different aryl bromides and chlorides. For example, the conversion of 2-chlorotoluene was 71% at 70 °C. During the catalytic reaction, the formation of Pd(0) nanoparticles was evidenced by TEM. Mechanistic studies, including Hg(0) tests, showed that Pd(0) nanoparticles acted as a source of catalytically active soluble palladium species.

  发现[IL] 2 [PdCl 4 ]类型的钯配合物（IL =咪唑阳离子）是2-溴甲苯与苯基硼酸在2-丙醇或2-丙醇/中进行的Suzuki-Miyaura反应的非常活泼的催化剂。使用常规加热或微波作为加热源在40°C的水中加热。在2-丙醇中，[dmiop] 2 [PdCl 4 ]和[dmdim] [PdCl 4 ]的收率最高（89％和85％）（dmiop = 1,2-二甲基-3-丙氧基甲基咪唑鎓阳离子，dmdim ＝ 3，3′-[1，7-（2，6-二氧杂庚烷）]双（1,2-二甲基咪唑鎓）阳离子，其含有在C2碳上被甲基取代的阳离子。在水的存在下，所有[IL] 2 [PdCl 4]复合物产生约。90％的2-甲基联苯 在不同的芳基溴化物和氯化物的Suzuki-Miyaura反应中也获得了很好的结果。例如，在70℃下2-氯甲苯的转化率为71％。在催化反应过程中，TEM证实了Pd（0）纳米颗粒的形成。
• CONDENSED CYCLIC COMPOUND, COMPOSITION INCLUDING THE CONDENSED CYCLIC COMPOUND, AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING CONDENSED CYCLIC COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20190229276A1

  公开（公告）日：2019-07-25

  A condensed cyclic compound represented by Formula 1: wherein in Formula 1, Ar 11 , Ar 12 , R 11 , R 12 , R 13 , and R 14 are the same as described in the specification.

  由式1表示的一种紧凑的环状化合物：其中在式1中，Ar11、Ar12、R11、R12、R13和R14与规范中描述的相同。
• Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines
  作者：Qianrong Li、Cong-Ying Zhou、Chengming Wang

  DOI：10.1021/acs.orglett.2c03808

  日期：2022.12.23

  number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed by insertion into biaryl isonitriles, thus leading to the rapid assembly of a variety of diversely functionalized 6-cyanoalkyl phenanthridines. A preliminary mechanism study revealed that a single-electron transfer radical process was possibly involved

  在无锡​​、过渡餐和无光条件下，通过可持续的 N-杂环卡宾催化产生了许多 γ-氰基烷基自由基，然后插入到联芳基异腈中，从而导致各种不同功能化的快速组装6-氰基烷基菲啶。初步的机理研究表明，可能涉及单电子转移自由基过程。