1-氯-4-(2-甲氧基苯基)苯 | 53824-23-0

• 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: 1-氯-4-(2-甲氧基苯基)苯
• 英文名称: 4'-chloro-2-methoxy-1,1'-biphenyl
• 英文别名: 2-methoxy-4'-chloro-1,1'-biphenyl；4'-chloro-2-methoxybiphenyl；4'-Chlor-2-methoxy-biphenyl；1-chloro-4-(2-methoxyphenyl)benzene
• CAS: 53824-23-0
• 化学式: C₁₃H₁₁ClO
• 分子量: 218.683
• InChiKey: MBOXSXIGVXMZDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-氯-4-(2-甲氧基苯基)苯 在 sodium dithionite 、 水 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 23.0h， 生成 N-[5-(sec-Butylamino-methyl)-4'-chloro-6-hydroxy-biphenyl-3-yl]-acetamide
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  4-(4-chlorophenyl)cyclohexane-1,3-dione 在 碘 、 铜 、 锌 、 三氯化磷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 15.0h， 生成 1-氯-4-(2-甲氧基苯基)苯
  参考文献：
  名称：

  非甾体抗炎药。3. 4'-氯-5-甲氧基-3-联苯基乙酸的位置异构体的合成及其抗炎和镇痛活性。

  摘要：

  4'-氯-5-甲氧基-3-联苯基乙酸的位置异构体3a-i [1（DKA-9），R = 4-ClPh; R'= MeO]是一种新开发的非甾体类抗炎药，已使用角叉菜胶诱导的大鼠爪水肿和AcOH扭体试验进行了抗炎和镇痛作用的评估。在这些测定中，与其他异构体相比，在结构上非常相似于1（R = 4-ClPh，R'= MeO）的3-和4-联苯基乙酸3a，d。但是，所测试的化合物均没有一个比1更具活性（R = 4-ClPh； R'= MeO）。在这一系列化合物中，良好的抗炎活性的结构要求似乎与镇痛活性的要求平行。

  DOI：

  10.1021/jm00140a019

文献信息

• Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis
  作者：Fengze Wang、Chen Wang、Guoping Sun、Gang Zou

  DOI：10.1016/j.tetlet.2019.151491

  日期：2020.2

  A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative

  低成本的二芳基硼酸与可分离的和潜在的芳族重氮鎓（即四氟硼酸酯和芳基三氮烯）的高效交叉偶联已在实用的钯催化剂体系下，在无碱条件下于室温下在敞口烧瓶中开发出来。通过使用0.3mol％的乙酸钯作为催化剂，可以以良好或优异的产率获得多种电子和空间上不同的联芳基，特别是那些带有配位邻位取代基的联芳基。该方案的特征包括二芳基硼酸的成本效益，对杂原子邻位取代底物的功效以及对芳基氯化物的高化学选择性，已在杀菌剂Boscalid的实际合成中得到了明确证明。
• Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings
  作者：Noriyasu Kataoka、Quinetta Shelby、James P. Stambuli、John F. Hartwig

  DOI：10.1021/jo025732j

  日期：2002.8.1

  aryl halides coupled with acyclic or cyclic secondary alkyl- and arylamines, with primary alkyl- and arylamines, and with aryl- and primary alkylboronic acids. These last couplings provide the first general procedure for reaction of terminal alkylboronic acids with aryl halides without toxic or expensive bases. The ligand not only generates highly active palladium catalysts, but it is air stable in

  已通过两步合成程序以高收率制备了五苯基二茂铁基二叔丁基膦，并且已研究了由带有该配体的配合物催化的各种交叉偶联过程的范围。该配体为芳基卤化物胺化和Suzuki偶联产生了非常普通的钯催化剂。对于未活化的芳基溴化物或氯化物的胺化，观察到的营业额约为1000。另外，该配体的络合物在温和条件下催化形成选定的芳基醚。反应包括富电子和贫电子的芳基溴化物和氯化物。在含有该配体的催化剂的存在下，这些芳基卤化物与无环或环状仲烷基和芳基胺，伯烷基和芳基胺，以及芳基和伯烷基硼酸偶联。这些最后的偶联为末端烷基硼酸与芳基卤化物的反应提供了第一个通用方法，而没有毒性或昂贵的碱。该配体不仅产生高活性的钯催化剂，而且在溶液和固态中都是空气稳定的。该配体的钯（0）配合物也具有空气稳定性，为固体，仅与溶液中的氧气缓慢反应。
• Catalyst for aromatic C—O, C—N, and C—C bond formation
  申请人：Yale University

  公开号：US06562989B2

  公开（公告）日：2003-05-13

  The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.

  本发明涉及一种过渡金属催化剂，包括一种第8族金属和具有结构的配体 其中R、R'和R"是具有1-15个碳原子的有机基团，n=1-5，m=0-4。本发明还涉及一种利用上述催化剂形成具有芳香性或乙烯基碳-氧、碳-氮或碳-碳键的化合物的方法。该催化剂和使用该催化剂的方法在大约室温和压力下的温和条件下制备化合物具有优势。
• Aromatic substitution. Part XXII. Polarity of aryl radicals
  作者：R. A. Abramovitch、O. A. Koleoso

  DOI：10.1039/j29690000779

  日期：——

  The rates of substitution of anisole relative to benzene by aryl radicals generated from diazonium tetrafluoroborates and pyridine in homogeneous solution have been measured and follow, qualitatively, the order expected on the basis of the theory of polarised aryl radicals. The substituent in the radical affects its permanent polarisation. Apparent contradictions in the literature concerning the behaviour

  已经测量了在均匀溶液中苯甲醚相对于苯的取代度，该取代度是由四氟硼酸重氮鎓和吡啶生成的芳基产生的，并且定性地遵循了基于极化芳基自由基理论的预期顺序。自由基中的取代基会影响其永久极化。文献中有关苯甲醚作为底物的行为和对甲氧基苯基自由基的极性的明显矛盾通过使用这种自由基源得以解决。如所预期的，对甲氧基苯基比苯基更具亲核性。间甲氧基苯基不比苯基更具亲电性，并提出了一个解释。p甲苯基是多个亲核比预期的基础上σ p -Me。
• A new precatalyst for the Suzuki reaction—a pyridyl-bridged dinuclear palladium complex as a source of mono-ligated palladium(<scp>0</scp>)
  作者：Andrew Beeby、Sylvia Bettington、Ian J. S. Fairlamb、Andrés E. Goeta、Anant R. Kapdi、Elina H. Niemelä、Amber L. Thompson

  DOI：10.1039/b401077a

  日期：——

  pyridyl-bridged palladium complex, trans-(P,N)-[PdBr(μ-C5H4N-C2,N)(PPh3)]21, was obtained from material isolated from the Suzuki cross-coupling reaction of 2-bromopyridine with 2,4-difluorophenylboronic acid in the presence of catalytic (PPh3)4Pd. Complex 1 is an effective precatalyst for the Suzuki cross-coupling reactions of a variety organoboronic acids and aryl bromides, and represents a useful source of mono-ligated

  双核 吡啶基-bridged钯络合物，反式- （P，Ñ） - [PDBR（μ -C 5 ħ 4 N-C 2，N）（PPH 3）] 2 1，从材料获得从的Suzuki交叉偶联反应中分离2-溴吡啶 和 2,4-二氟苯基硼酸在催化（PPh 3）4 Pd的存在下。配合物1是多种有机硼酸和芳基溴化物的Suzuki交叉偶联反应的有效前催化剂，并且代表单连接钯（0）“（Ph 3 P）Pd（0）”的有用来源。