3,5-difluoro-4'-methyl-1,1'-biphenyl

• 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: 3,5-difluoro-4'-methyl-1,1'-biphenyl
• 英文别名: 3,5-difluoro-4'-methylbiphenyl；4-Methyl-3',5'-difluorbiphenyl；1,3-difluoro-5-(4-methylphenyl)benzene
• 化学式: C₁₃H₁₀F₂
• 分子量: 204.219
• InChiKey: GQEKCTAHFDPTQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-difluoro-4'-methyl-1,1'-biphenyl 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydroxide 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 2-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-5-(3',5'-difluorobiphenyl-4-ylmethylsulfanyl)-[1,3,4]oxadiazol
  参考文献：
  名称：

  Structure-based optimization of oxadiazole-based GSK-3 inhibitors

  摘要：

  Inhibition of glycogen synthase kinase-3 (GSK-3) induces neuroprotective effects, e.g. decreases beta-amyloid production and reduces tau hyperphosphorylation, which are both associated with Alzheimer's disease (AD). The two isoforms of GSK-3 in mammalians are GSK-3 alpha and beta, which share 98% homology in their catalytic domains. We investigated GSK-3 inhibitors based on 2 different scaffolds in order to elucidate the demands of the ATP-binding pocket [1]. Particularly, the oxadiazole scaffold provided potent and selective GSK-3 inhibitors. For example, the most potent inhibitor of the present series, the acetamide 26d, is characterized by an IC50 of 2 nM for GSK-3 alpha and 17 nM for GSK-3 beta. In addition, the benzodioxane 8g showed up to 27-fold selectivity for GSK-3 alpha over GSK-3 beta, with an IC50 of 35 nM for GSK-3 alpha. Two GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay to evaluate simultaneously permeability and safety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.006
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 180.0 ℃ 、6.67 Pa 条件下， 反应 0.25h， 生成 3,5-difluoro-4'-methyl-1,1'-biphenyl
  参考文献：
  名称：

  Brune, Hans-Albert; Hess, Reiner; Schmidtberg, Guenther, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 12, p. 1772 - 1780

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED TRICYCLIC AMIDES, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] AMIDES TRICYCLIQUES SUBSTITUÉS, ANALOGUES DE CEUX-CI ET PROCÉDÉS LES METTANT EN OEUVRE
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2021229302A1

  公开（公告）日：2021-11-18

  The present disclosure includes substituted tricyclic amides, or analogues thereof of formula (I) (I), wherein X, Y, ring A, R1, R5, R6 and R7 are as defined herein, and compositions comprising compounds of formula (I) that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.

  本公开涵盖了替代三环酰胺，或其类似物的化合物，其化学式为(I)，其中X、Y、环A、R1、R5、R6和R7如本文所定义，并包括化合物(I)的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。
• BIMESOGENIC COMPOUNDS AND MESOGENIC MEDIA
  申请人：Merck Patent GmbH

  公开号：US20170210990A1

  公开（公告）日：2017-07-27

  The invention relates to bimesogenic compounds of formula I wherein R 11 , R 12 , MG 11 , MG 12 , X 11 , X 12 and Sp 1 have the meaning given in claim 1 , to the use of bimesogenic compounds of formula I in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

  这项发明涉及式I的双向嵌段化合物，其中R11、R12、MG11、MG12、X11、X12和Sp1的含义如权利要求1所述，涉及在液晶介质中使用式I的双向嵌段化合物，特别涉及包括根据本发明的液晶介质的柔电液晶器件。
• Nickel- and Palladium-Catalyzed Cross-Coupling Reaction of Polyfluorinated Arenes and Alkenes with Grignard Reagents
  作者：Tomoyuki Saeki、Kohei Tamao、Yohei Takashima

  DOI：10.1055/s-2005-871571

  日期：——

  The cross-coupling reaction of fluorobenzene with an aryl Grignard reagent has been reinvestigated which revealed that the reaction readily proceeds under ordinary conditions using a catalytic amount of NiCl2(dppp) even at room temperature. The use of nickel catalysts and Grignard reagent is essential for the activation of the carbon-fluorine bond. The palladium catalyst is also effective for the 1,2-difluorobenzene and trifluorobenzenes to selectively produce the corresponding mono-coupled products while the nickel-based catalyst system affords a mixture of the mono-coupled product and di- or tri-coupled product.

  氟苯与芳基格里尼亚试剂的交叉偶联反应已被重新研究，结果表明在普通条件下，即使在室温下也能通过使用催化量的NiCl2(dppp)容易地进行反应。使用镍催化剂和格里尼亚试剂对于激活碳-氟键是至关重要的。钯催化剂对于1,2-二氟苯和三氟苯也有效，能够选择性地产生相应的单偶联产物，而基于镍的催化剂系统则会产生单偶联产物和双偶联或三偶联产物的混合物。
• Direct C–H Carboxylation Forming Polyfunctionalized Aromatic Carboxylic Acids by Combined Brønsted Bases
  作者：Masanori Shigeno、Kazuya Hanasaka、Itsuki Tohara、Koki Izumi、Hiroyuki Yamakoshi、Eunsang Kwon、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.1c03866

  日期：2022.1.28

  CO2 fixation into electron-deficient aromatic C–H bonds proceeds with the combined Brønsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromatic carboxylic acids.

  在 CO 2气氛下，通过组合的布朗斯台德碱 LiO- t -Bu 和 LiO- t -Am/CsF/18-crown-6 ( t -Am = CEtMe 2 ) 将CO 2固定成缺电子芳族 C-H 键以提供多种多官能化芳族羧酸。
• Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of <i>N</i>-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides
  作者：Takuji Hatakeyama、Sigma Hashimoto、Kentaro Ishizuka、Masaharu Nakamura

  DOI：10.1021/ja9039289

  日期：2009.8.26

  halides (Ar(2)X) to give unsymmetrical biaryls (Ar(1)-Ar(2)). Iron fluorides in combination with SIPr, a saturated NHC ligand, catalyze the biaryl cross-coupling between various aryl chlorides and aryl Grignard reagents in high yield and high selectivity. On the other hand, cobalt and nickel fluorides in combination with IPr, an unsaturated NHC ligand, exhibit interesting complementary reactivity in the

  N-杂环卡宾 (NHC) 和铁族金属（Fe、Co 和 Ni）的氟化物盐的组合已被证明是芳基格氏试剂 (Ar(1)MgBr) 交叉偶联反应的极好催化剂与芳基和杂芳基卤化物 (Ar(2)X) 生成不对称的联芳基化合物 (Ar(1)-Ar(2))。氟化铁与饱和 NHC 配体 SIPr 结合以高产率和高选择性催化各种芳基氯化物和芳基格氏试剂之间的联芳基交叉偶联。另一方面，钴和镍氟化物与不饱和 NHC 配体 IPr 结合，在芳基溴化物或碘化物的偶联中表现出有趣的互补反应性；相反，对于这些底物，铁催化剂表现出较低的选择性。在大多数情况下，通过选择合适的金属氟化物/NHC 组合，均耦合副产物的形成被显着抑制到低于 5%。本催化剂组合提供优于现有方法的几个合成优势：在不使用钯催化剂和膦配体的情况下实际合成范围广泛的不对称联芳基化合物。在化学计量控制实验和理论研究的基础上，氟化物反离子独特催化作用的起源可以归因于形成高价杂配金属盐