3-cyano-2'-methylbiphenyl | 253678-80-7

• 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: 3-cyano-2'-methylbiphenyl
• 英文别名: 2'-methyl-[1,1'-biphenyl]-3-carbonitrile；2'-methylbiphenyl-3-carbonitrile；3-(2'-tolyl)benzonitrile；2'-Methyl[1,1'-biphenyl]-3-carbonitrile；3-(2-methylphenyl)benzonitrile
• CAS: 253678-80-7
• 化学式: C₁₄H₁₁N
• mdl: MFCD05979142
• 分子量: 193.248
• InChiKey: YWZPKVVVOMUEIE-UHFFFAOYSA-N

物化性质

• 沸点：
  321.6±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：
  0.071
• 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：

  3-cyano-2'-methylbiphenyl 在 N-溴代丁二酰亚胺(NBS) 、 羟胺 、 乙酸酐 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 三氟乙酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2'-[({4-[1-(1-Imino-ethyl)-piperidin-4-yloxy]-phenyl}-methanesulfonyl-amino)-methyl]-biphenyl-3-carboxamidine
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  间溴苯甲腈 、 o-tolyltris(2-propoxy)titanium 在 N-(diphenylphosphino)-2-phenyl-1H-indole 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 1.08h， 以90%的产率得到3-cyano-2'-methylbiphenyl
  参考文献：
  名称：

  使用有机钛亲核试剂进行钯催化的芳基卤化物的交叉偶联

  摘要：

  它们构成了很好的一对：由Pd（OAc）2和吲哚基膦配体生成的催化剂在钛介导的芳基卤化物偶联中非常有效。可以使用低至0.05 mol％Pd的催化剂负载量。温和的反应条件还使芳基磺酰氯与芳基钛试剂偶合生成二芳基砜。

  DOI：

  10.1002/anie.200904033

文献信息

• A simple, efficient and recyclable phosphine-free catalytic system for Suzuki–Miyaura reaction of aryl bromides
  作者：Hong Zhao、Jian Peng、Ruian Xiao、Mingzhong Cai

  DOI：10.1016/j.molcata.2011.01.014

  日期：2011.3

  The Suzuki–Miyaura reaction of aryl bromides using 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(II)] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the Suzuki–Miyaura reaction of aryl bromides with arylboronic acids providing good to excellent yield of the desired products. This heterogeneous

  描述了使用3-（2-氨基乙基氨基）丙基官能化的MCM-41固定的钯（II）配合物[MCM-41-2N-Pd（II）]作为有效的多相催化剂的芳基溴化物的Suzuki-Miyaura反应。已发现开发的催化系统对于芳基溴化物与芳基硼酸的Suzuki-Miyaura反应有效，可提供所需产物的良好或优异的收率。这种多相钯催化剂可以重复使用至少10次，而不会降低活性。我们的系统不仅避免使用膦配体，而且解决了钯催化剂回收和再利用的基本问题。
• Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes
  作者：Zhenxing Xi、Yongbo Zhou、Wanzhi Chen

  DOI：10.1021/jo8018686

  日期：2008.11.7

  nickel-N-heterocyclic carbene catalyzed Negishi cross-coupling reaction of a variety of unactivated aryl chlorides, heterocyclic chlorides, aryl dichlorides, and vinyl chloride. The mononuclear and binuclear nickel-NHC complexes supported by heteroarene-functionalized NHC ligands are found to be highly efficient for the coupling of unactivated aryl chlorides and organozinc reagents, leading to biaryls and terphenyls

  我们描述了各种未活化的芳基氯化物，杂环氯化物，芳基二氯化物和氯乙烯的第一个镍-N-杂环卡宾催化的Negishi交叉偶联反应。发现杂芳烃官能化的NHC配体支持的单核和双核镍-NHC络合物对于未活化的芳基氯化物和有机锌试剂的偶联非常有效，在温和的条件下可产生联芳基和三联苯，收率高至优异。对于所有的芳基氯化物，由于可能的双金属协同作用，双核镍催化剂显示出比单核镍配合物更高的活性。
• An Efficient Class of P,N-Type “PhMezole-phos” Ligands: Applications in Palladium-Catalyzed Suzuki Coupling of Aryl Chlorides
  作者：Shun Man Wong、Chau Ming So、Kin Ho Chung、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/ejoc.201200355

  日期：2012.8

  describes an efficient class of hemilabile benzimidazolyl–phosphane ligands that can be easily accessed from commercially available and inexpensive starting materials. The application of this ligand array in the palladium-catalyzed Suzuki–Miyaura coupling reaction of aryl chlorides with arylboronic acids is described. The palladium catalyst generated from this hemilabile phosphane is highly effective

  本研究描述了一类有效的苯并咪唑基磷烷配体，可以从市售且廉价的起始材料中轻松获得。描述了该配体阵列在钯催化的芳基氯化物与芳基硼酸的 Suzuki-Miyaura 偶联反应中的应用。由这种半稳定性磷烷生成的钯催化剂在未活化的芳基氯化物的 Suzuki-Miyaura 偶联中非常有效，并且可以实现低至 1 ppm 的催化剂负载量。
• Remarkably Effective Phosphanes Simply with a PPh₂Moiety: Application to Pd-Catalysed Cross-Coupling Reactions for Tetra-<i>ortho</i>-substituted Biaryl Syntheses
  作者：Chau Ming So、Wing Kin Chow、Pui Ying Choy、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201000723

  日期：2010.7.19

  Expanding the horizons of ArPPh2: New applications of triarylphosphane ligands are presented. The Pd–L1 and Pd–L2 complexes offer exceptionally high activity in Suzuki–Miyaura cross‐couplings of aryl chlorides. The extremely congested synthesis of tetra‐ortho‐substituted biaryl compounds is achieved for the first time by simply using triarylphosphane ligands.

  扩展ArPPh 2的视野：提出了三芳基膦配体的新应用。Pd– L1和Pd– L2络合物在Suzuki-Miyaura芳基氯化物的交叉偶联中具有极高的活性。仅通过使用三芳基膦配体，就可以实现四邻位取代的联芳基化合物的极为拥挤的合成。
• Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles
  作者：Aiichiro Nagaki、Daisuke Ichinari、Jun-ichi Yoshida

  DOI：10.1021/ja5071762

  日期：2014.9.3

  carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature-residence time mapping is responsible for the success of the present transformation. The present method

  建立了一种基于闪速化学的苯三组分偶联流动微反应器方法。由 1-溴-2-碘苯产生的邻溴苯基锂和由相应芳基卤化物产生的官能化芳基锂在 -70 °C 下混合。在随后的反应器中，邻溴苯基锂在 -30°C 下分解生成苄基而不影响官能化的芳基锂，并且苄基与芳基锂的碳锂化反应自发发生。所得官能化联芳基锂在随后的反应器中与亲电试剂反应，得到相应的三组分偶联产物。使用温度-停留时间映射对反应条件进行精确优化是目前转化成功的原因。