4-(2-methoxybenzyl)pyridine | 35854-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-methoxybenzyl)pyridine
• 英文别名: 4-o-Methoxybenzylpyridin；4-(o-Methoxybenzyl)pyridine；4-[(2-methoxyphenyl)methyl]pyridine
• CAS: 35854-36-5
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: DKQCOVWISMHGLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-methoxybenzyl)pyridine 、 碘甲烷 在 sodium tetrahydroborate 作用下， 生成 4-(2-Methoxy-benzyl)-1-methyl-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation

  摘要：

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.

  DOI：

  10.1021/jm00174a007
• 作为产物：
  描述：

  α-(2-methoxyphenyl)-4-pyridinemethanol 在 甲酸 、 锌 作用下， 反应 16.0h， 以80%的产率得到4-(2-methoxybenzyl)pyridine
  参考文献：
  名称：

  Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation

  摘要：

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.

  DOI：

  10.1021/jm00174a007

文献信息

• Synthesis of 4-benzylpyridines via Pd-catalyzed CH₃-arylation of 4-picoline
  作者：Jing Wu、Dadian Wang、Xiang Chen、Qingwen Gui、Hua Li、Ze Tan、Genping Huang、Guangwei Wang

  DOI：10.1039/c7ob01726j

  日期：——

  A highly efficient synthesis of 4-benzylpyridines was developed via Pd-catalyzed C(sp³)–H arylation between 4-picoline and aryl halides. It was found that the best yields were achieved with a simple Pd(PPh₃)₄ catalyst and Cs₂CO₃ as the base.

  通过Pd催化的4-苯甲基吡啶的合成，通过4-哌啶和芳基卤化物之间的C(sp3)-H芳基化反应进行。发现最佳产率是使用简单的Pd(PPh3)4催化剂和Cs2CO3作为碱。
• EFANGE, S. M. N.;MICHELSON, R. H.;REMMEL, R. P.;BOUDREAU, R. J.;DUTTA, A.+, J. MED. CHEM., 33,(1990) N2, C. 3133-3138
  作者：EFANGE, S. M. N.、MICHELSON, R. H.、REMMEL, R. P.、BOUDREAU, R. J.、DUTTA, A.+

  DOI：——

  日期：——
• [EN] QUINUCLIDINE DERIVATIVES AS SQUALENE SYNTHASE INHIBITORS<br/>[FR] DERIVES DE QUINUCLIDINE EN TANT QU'INHIBITEURS DE SQUALENE SYNTHASE
  申请人：ZENECA LIMITED

  公开号：WO1995035295A1

  公开（公告）日：1995-12-28

  (EN) Compounds of formula (I) wherein R1 is hydrogen or hydroxy; R2 is hydrogen; or R1 and R2 are joined together so that CR1 -CR2 is a double bond; X is selected from -CH2CH2-, -CH = CH-, -C $m(0) C-, -CH2O-, -CH2NH-, -NHCH2-, -CH2CO-, -COOH2-, -CH2S(O)n- and -S(O)nCH2- (wherein n is 0,1 or 2); Ar is phenyl which bears one or more substituents independently selected from the groups alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxyalkyl, alkylamino, di-[alkyl]amino, carbamoyle, alkylcarbamoyl, di-[alkyl]carbamoyl, alkanoyl and oxime derivatives thereof and 0-alkyl ethers of said oximes, alkylthio, alkylsulphinyl and alkylsulphonyl when substituted by one or more groups selected from heterocyclyl, heterocyclyloxy and heterocyclyloxycarbonyl; or Ar is phenyl which bears one or more heterocyclyloxy groups; and wherein Ar and/or a phenyl or heterocyclyl moiety in any of said groups mentioned above may further be substituted; and their pharmaceutically acceptable salts inhibits squalene synthase and are hence useful in lowering cholesterol levels in blood plasma. Processes for preparing compounds of formula (I) are also referred to as well as pharmaceutical compositions containing them and their use in medicine.(FR) Composés de la formule (I) ainsi que leurs sels acceptables sur le plan pharmacologique. Dans cette formule, R1 représente hydrogène ou hydroxy; R2 représente hydrogène; ou bien R1 et R2 sont joints de manière à ce que CR1-CR2 représente une liaison double; X est choisi parmi -CH2CH2-, -CH=CH-, -C$m(Z)C-, -CH2O-, -CH2NH-, -NHCH2-, -CH2CO-, -COOH2-, -CH2S(O)n- et -S(O)nCH2- (dans lesquels n vaut 0, 1 ou 2); Ar représente phényle qui porte un ou plusieurs substituants choisis indépendamment parmi les groupes alcoyle, alcényle, alcynyle, alcoxy, alcoxycarbonyle, alcoxycarbonylalcoyle, alcoxyalcoyle, alcoylamino, di-[alcoyl]amino, carbamoyle, alcoylcarbamoyle, di-[alcoyle]carbamoyle, alcanoyle, parmi des dérivés oximes de ces groupes et des éthers de 0-alcoyle de ces oximes, alcoylthio, alcoylsulfinyle et alcoylsulfonyle lors d'une substitution par un ou plusieurs groupes choisis parmi hétérocyclyle, hétérocyclyloxy et hétérocyclyloxycarbonyle; ou bien Ar représente phényle qui porte un ou plusieurs groupes hétérocyclyloxy; et Ar et/ou une fraction phényle ou hétérocyclyle dans l'un quelconque des groupes mentionnés ci-dessus peut être à nouveau substitué. Ces composés inhibent la squalène synthase et, par conséquent, sont utiles pour abaisser les taux de cholestérol dans le plasma sanguin. L'invention concerne également des procédés de préparation des composés de la formule (I), de même que des compositions pharmaceutiques contenant ces composés et l'utilisation de ceux-ci en médecine.
• Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation
  作者：S. Mbera Ngale Efange、R. H. Michelson、R. P. Remmel、R. J. Boudreau、A. K. Dutta、A. Freshler

  DOI：10.1021/jm00174a007

  日期：1990.12

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.