3-甲氧基-3'-甲基-1,1'-联苯 | 81722-84-1

• 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: 3-甲氧基-3'-甲基-1,1'-联苯
• 英文名称: 3-methoxy-3'-methyl-1,1'-biphenyl
• 英文别名: 3-methoxy-3'-methylbiphenyl；1-methoxy-3-(3-methylphenyl)benzene
• CAS: 81722-84-1
• 化学式: C₁₄H₁₄O
• mdl: MFCD06802355
• 分子量: 198.265
• InChiKey: NRGRNDDCMMAYPV-UHFFFAOYSA-N

物化性质

• 沸点：
  302.8±11.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-甲氧基-3'-甲基-1,1'-联苯 在 氢碘酸 作用下， 反应 2.0h， 以90%的产率得到3'-甲基-3-联苯醇
  参考文献：
  名称：

  Cyclohexylcarbamic Acid 3‘- or 4‘-Substituted Biphenyl-3-yl Esters as Fatty Acid Amide Hydrolase Inhibitors:  Synthesis, Quantitative Structure−Activity Relationships, and Molecular Modeling Studies

  摘要：

  Fatty acid amide hydrolase (FAAH) is a promising target for modulating endocannabinoid and fatty acid ethanolamide signaling, which may have important therapeutic potential. We recently described a new class of O-arylcarbamate inhibitors of FAAH, including the cyclohexylcarbamic acid biphenyl-3-yl ester URB524 (half-maximal inhibitory concentration, IC50 = 63 nM), which have significant anxiolytic-like properties in rats. In the present study, by introducing a selected group of substituents at the meta and para positions of the distal phenyl ring of URB524, we have characterized structure-activity profiles for this series of compounds and shown that introduction of small polar groups in the meta position greatly improves inhibitory potency. Most potent in the series was the m-carbamoyl derivative URB597 (4i, IC50 = 4.6 nM). Furthermore, quantitative structure-activity relationship (QSAR) analysis of an extended set of meta-substituted derivatives revealed a negative correlation between potency and lipophilicity and suggested that small-sized substituents may undertake polar interactions with the binding pocket of the enzyme. Docking studies and molecular dynamics simulations, using the crystal structure of FAAH, indicated that the O-biphenyl scaffold of the carbamate inhibitors can be accommodated within a lipophilic region of the substrate-binding site, where their folded shape mimics the initial 10-12 carbon atoms of the arachidonyl moiety of anandamide (a natural FAAH substrate) and methyl arachidonyl fluorophosphonate (a nonselective FAAH inhibitor). Moreover, substituents at the meta position of the distal. phenyl ring can form hydrogen bonds with atoms located on the polar section of a narrow channel pointing toward the membrane-associated side of the enzyme. The structure-activity characterization reported here should help optimize the pharmacodynamic and pharmacokinetic properties of this class of compounds.

  DOI：

  10.1021/jm031140x
• 作为产物：
  描述：

  (3-methoxyphenyl)magnesium bromide 在 cis-Chloro(3-methylphenyl)bis(triphenylphosphan)platin(II) 作用下， 生成 3-甲氧基-3'-甲基-1,1'-联苯
  参考文献：
  名称：

  Brune, Hans Albert; Ertl, Josef; Grafl, Dieter, Chemische Berichte, 1982, vol. 115, # 3, p. 1141 - 1153

  摘要：

  DOI：

文献信息

• <i>N</i>-Heterocyclic Carbene Coordinated Heterogeneous Pd Nanoparticles as Catalysts for Suzuki–Miyaura Coupling
  作者：Hyemin Min、Hiroyuki Miyamura、Shū Kobayashi

  DOI：10.1246/cl.160369

  日期：2016.7.5

  Palladium nanoparticle (Pd NP) catalysts immobilized in a polymer with an N-heterocyclic carbene (NHC) moiety (PICB-NHC-Pd) have been developed, wherein the NHC moiety plays dual roles as a crosslinker and a ligand to activate the Pd NPs. The presence of both Pd NPs and NHC was confirmed by STEM/EDS and SR-MAS NMR analyses, respectively. This PICB-NHC-Pd catalyst showed excellent activity in the Suzuki–Miyaura

  已开发出固定在具有 N-杂环卡宾 (NHC) 部分 (PICB-NHC-Pd) 的聚合物中的钯纳米颗粒 (Pd NP) 催化剂，其中 NHC 部分起着交联剂和配体的双重作用以激活 Pd NP . 分别通过 STEM/EDS 和 SR-MAS NMR 分析证实了 Pd NPs 和 NHC 的存在。这种 PICB-NHC-Pd 催化剂在 Suzuki-Miyaura 偶联反应中表现出优异的活性，而不会浸出 Pd。在克级合成中获得了优异的结果，并且在不损失催化剂活性的情况下完成了催化剂回收/再利用实验。
• Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
  作者：Qing He、Liwen Wang、Yong Liang、Zunting Zhang、Stanislaw F. Wnuk

  DOI：10.1021/acs.joc.6b01648

  日期：2016.10.7

  Transition-metal-free LiCl-promoted cross-coupling reactions of tetraphenyltin, trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylstannanes with aryl halides in DMF provided access to biaryls in good to high yields. Up to four phenyl groups were transferred from the organostannanes substrates. The aryls bearing electron-withdrawing groups in either halides or organotin substrates gave coupling

  四苯基锡，三氯苯基，二氯二苯基和氯代三苯基锡与芳基卤化物在DMF中的无过渡金属LiCl促进的交叉偶联反应提供了以高收率获得高收率的联芳基的途径。从有机锡烷底物中转移了最多四个苯基。在卤化物或有机锡基质中带有吸电子基团的芳基以较高的收率得到偶联产物。该方法已被用于有效合成异丙基黄酮。
• Bidentate P, N−P Ligand for Nickel-Catalyzed Cross-Coupling of Aryl or Benzyl Chlorides with ArMgX
  作者：Raju Ghosh、Amitabha Sarkar

  DOI：10.1021/jo1016458

  日期：2010.12.3

  cross-coupling reaction of a variety of aryl, heteroaryl, and benzyl chlorides with ArMgX is catalyzed by 2 mol % of a nickel−phosphine complex prepared in situ from an equimolar amount of Ni(CH3CN)2Cl2 and ligand (L2) to yield products in excellent yield in THF at room temperature. This new bidentate ligand (L2) is stable in air and forms a stable complex upon reaction with Ni(CH3CN)2Cl2. Structures of the

  各种芳基，杂芳基和苄基氯与ArMgX的交叉偶联反应由2摩尔％从等摩尔量的Ni（CH 3 CN）2 Cl 2和配体（ L2），以在室温下以优异的THF收率得到产物。该新的双齿配体（L2）在空气中稳定，并且在与Ni（CH 3 CN）2 Cl 2反应时形成稳定的络合物。配体和配合物的结构通过单晶X射线衍射确认。
• Gold-catalyzed synthesis of 1,3-disubstituted benzenes through tandem allylation/cyclization reaction of alkynals
  作者：Sabyasachi Bhunia、Shariar Md. Abu Sohel、Chao-Chin Yang、Shie-Fu Lush、Fwu-Ming Shen、Rai-Shung Liu

  DOI：10.1016/j.jorganchem.2008.10.049

  日期：2009.2

  Treatment of alkynals with 2-substituted allylsilanes and PPh3AuCl/AgOTf (5/3 mol%) catalyst led to formation of 1,3-disubstituted benzenes efficiently. This reaction sequence comprises an initial allylation of aldehyde, followed by cycloisomerization of enynes; PPh3AuOTf is active in both steps.

  用2-取代的烯丙基硅烷和PPh 3 AuCl / AgOTf（5/3 mol％）催化剂处理炔烃可有效地形成1,3-二取代的苯。该反应顺序包括醛的初始烯丙基化，然后是烯炔的环异构化。PPh 3 AuOTf在两个步骤中均处于活动状态。
• [EN] PIPERAZINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLU5 RECEPTORS<br/>[FR] DÉRIVÉS DE PIPÉRAZINE ET LEUR UTILISATION À TITRE DE MODULATEURS ALLOSTÉRIQUES POSITIFS DES RÉCEPTEURS MGLUR5
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013087805A1

  公开（公告）日：2013-06-20

  This invention relates to compounds of formula (I) their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. R1, R2, R3, R4, Q have meanings given in the description.

  这项发明涉及公式(I)化合物，它们作为mGlu5受体活性的正向变构调节剂的用途，含有这些化合物的药物组合物，以及将其用作治疗和/或预防与谷氨酸功能障碍相关的神经和精神障碍，如精神分裂症或认知功能下降，如痴呆症或认知障碍的药剂的方法。R1、R2、R3、R4、Q在描述中有给定的含义。