4-甲基-2-(2-甲基苯基)吡啶 | 64291-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-甲基-2-(2-甲基苯基)吡啶
• 英文名称: 4-methyl-2-(o-tolyl)pyridine
• 英文别名: 4-Methyl-2-(2-methylphenyl)pyridine
• CAS: 64291-98-1
• 化学式: C₁₃H₁₃N
• mdl: MFCD09031940
• 分子量: 183.253
• InChiKey: DECZVBVDSWDZBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-甲基-2-(2-甲基苯基)吡啶 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Discovery of 4-{4-[3-(Pyridin-2-yl)-1H-pyrazol-4-yl]pyridin-2-yl}-N-(tetrahydro-2H- pyran-4-yl)benzamide (GW788388):  A Potent, Selective, and Orally Active Transforming Growth Factor-β Type I Receptor Inhibitor

  摘要：

  Inhibitors of transforming, growth factor beta (TGF-beta) type I receptor (ALK5) offer a novel approach for the treatment of fibrotic diseases Such as renal, hepatic, and pulmonary fibrosis. The optimization of a novel phenylpyridine pyrazole series (1a) led to the identification of potent, selective, and orally active ALK5 inhibitors. The cellular potency and pharmacokinetics profiles of these derivatives were improved and several compounds presented antifibrotic activity when orally administered to rats in an acute liver model of dimethylnitrosamine- (DMN-) induced expression of collagen IA1 mRNA, a major gene contributing to excessive extra cellular matrix deposit. One of the most potent ALK5 inhibitors identified in this chemical series, Compound 13d (GW788388), reduced the expression of collagen IA1 by 80% at a dose of I mg/kg, twice a day (b.i.d.). This compound significantly reduced the expression of collagen IAI mRNA when administered orally at 10 mg/kg once a day (u.i.d.) in a model of puromycin aminonucleoside-induced renal fibrosis.

  DOI：

  10.1021/jm0509905
• 作为产物：
  描述：

  4-甲基吡啶 生成 4-甲基-2-(2-甲基苯基)吡啶
  参考文献：
  名称：

  PROSTAKOV N. S.; PLESHAKOV V. G.; SEJTEMBETOV T. S.; FESENKO D. A.; ONASA+, ZH. ORGAN. XIMII, 1977, 13, 7, 1484-

  摘要：

  DOI：

文献信息

• METHOD OF PRODUCING AROMATIC COMPOUND
  申请人：Kakiuchi Fumitoshi

  公开号：US20090043096A1

  公开（公告）日：2009-02-12

  A method of producing an aromatic compound of the following formula (3) comprising reacting a compound of the following formula (1) with an olefin compound of the following formula (2) in the presence of a transition metal complex: (wherein, an Ar 1 ring represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, an Ar 2 ring represents a heterocyclic ring containing X 1 and N*, and the X 1 represents a nitrogen atom or carbon atom and the N represents a nitrogen atom connecting via a double bond to either one of two adjacent atoms in the Ar 2 ring.) (wherein, R 1 , R 2 , R 3 and R 4 represent each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 18 carbon atoms.) (wherein, Ar 1 , Ar 2 , X 1 , N*, R 1 , R 2 and R 3 represent the same meanings as described above.).

  一种制备具有以下式（3）的芳香化合物的方法，包括在过渡金属配合物的存在下，将具有以下式（1）的化合物与具有以下式（2）的烯烃化合物反应：（其中，Ar1环代表芳香烃环或芳香杂环，Ar2环代表含有X1和N*的杂环，X1代表氮原子或碳原子，N代表氮原子，通过双键连接到Ar2环中的两个相邻原子中的任意一个。）（其中，R1、R2、R3和R4分别代表氢原子、具有1至10个碳原子的烷基基团或具有6至18个碳原子的芳基基团。）（其中，Ar1、Ar2、X1、N*、R1、R2和R3的含义与上述描述相同。）
• Kumada-Corriu Cross-Couplings with 2-Pyridyl Grignard Reagents
  作者：Lutz Ackermann、Harish K. Potukuchi、Anant R. Kapdi、Carola Schulzke

  DOI：10.1002/chem.201000032

  日期：2010.3.15

  SPOs meet the challenge: A palladium complex derived from air‐ and moisture‐stable secondary phosphine oxide (SPO) (1‐Ad)2P(O)H enables general cross‐coupling reactions of challenging electron‐deficient 2‐pyridyl Grignard reagents with ample scope (see scheme).

  SPO迎接挑战：由空气和湿气稳定的次生氧化膦（SPO）（1-Ad）2 P（O）H衍生的钯配合物可实现具有挑战性的缺乏电子的2-吡啶基格氏试剂与范围足够（请参阅方案）。
• Regioselective Sequential Silylation and Borylation of Aromatic Aldimines as a Strategy for Programming Synthesis of Multifunctionalized Benzene Derivatives
  作者：Masahito Murai、Naoki Nishinaka、Takahiro Enoki、Kazuhiko Takai

  DOI：10.1021/acs.orglett.9b04338

  日期：2020.1.3

  Regioselective difunctionalization of two different C-H bonds in one pot using a three-component coupling reaction is described. The reaction order is important for controlling the reactivity and regioselectivity, and the first silylation promotes the second borylation. The introduced formyl, silyl, and boryl functional groups could be independently converted to other functional groups, and the substitution

  描述了使用三组分偶联反应在一个罐中两个不同的CH键的区域选择性双官能化。反应顺序对于控制反应性和区域选择性很重要，并且第一次甲硅烷基化促进了第二次硼化。引入的甲酰基，甲硅烷基和硼烷基官能团可独立地转化为其他官能团，并且所得苯的取代模式难以通过常规方法获得。
• Rh(III)-Catalyzed C–H Alkylation of Arenes Using Alkylboron Reagents
  作者：He Wang、Songjie Yu、Zisong Qi、Xingwei Li

  DOI：10.1021/acs.orglett.5b01232

  日期：2015.6.5

  alkylation of arenes using commercially available alkyltrifluoroborates is disclosed. Oximes, heteroarenes, azomethines, N-nitrosoamines, and amides are viable directing groups to entail this transformation. The alkyl group in the boron reagent can be extended to primary alkyls, benzyl, and cycloalkyls, and the reaction proceeded with controllable mono- and dialkylation selectivity when both ortho C–H

  公开了使用可商购的烷基三氟硼酸酯的铑（III）催化的芳烃直接烷基化。肟，杂芳烃，偶氮甲碱，N-亚硝基胺和酰胺是进行这种转化的可行的导向基团。硼试剂中的烷基可以扩展为伯烷基，苄基和环烷基，当两个邻位C-H位都可访问时，反应以可控的单烷基化和二烷基化选择性进行。
• Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp²)–H arylation
  作者：Qian Wu、Chenglong Du、Yumin Huang、Xingyan Liu、Zhen Long、Feijie Song、Jingsong You

  DOI：10.1039/c4sc02070g

  日期：——

  and 3b) and [AuBr(Ph)(tpy)] (7), as well as the aryl gold(III) complex [AuCl2(Ph)(tpy)] (8) (tpy = 2-(o-tolyl)pyridine) as reliable models, we present a detailed study of the mechanism for gold(III)-catalyzed oxidative cross-coupling reactions between cycloaurable arenes and arylboronic acids. Here we report the direct evidence for a mechanistic proposal including arene C–H activation, transmetallation

  基于明确的五元芳基金 ( III ) 配合物，[Au(tpy)X 2 ] ( 3a和3b ) 和 [AuBr(Ph)(tpy)] ( 7 )，以及芳基金 ( III ) 配合物 [AuCl 2 (Ph)(tpy)] ( 8 ) (tpy = 2-( o -tolyl)pyridine) 作为可靠的模型，我们对金 ( III ) 催化的氧化交叉反应机理进行了详细研究。可环芳芳烃和芳基硼酸之间的偶联反应。在这里，我们报告了机制建议的直接证据，包括芳烃 C-H 活化、金属转移和联芳基还原消除。螯合辅助的 C-H 活化策略已用于开发金 ( III ) 催化的芳烃与芳基试剂的 C-H 键芳基化，以形成扩展的 π 共轭体系。