2-(2-methyl-6-styrylphenyl)-pyridine | 945721-46-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(2-methyl-6-styrylphenyl)-pyridine
• 英文别名: 2-[2-methyl-6-(2-phenylethenyl)phenyl]pyridine
• CAS: 945721-46-0
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: WNXOOUGYKCNJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙醛 在 4-二甲氨基吡啶 、 (η6-1,3,5-cyclooctatriene)(η4-1,5-cyclooctadiene)ruthenium(0) 、 三乙胺 作用下， 以 四氢呋喃 、 对二甲苯 为溶剂， 反应 24.0h， 生成 2-(2-methyl-6-styrylphenyl)-pyridine
  参考文献：
  名称：

  Ruthenium-catalyzed Ortho-selective Aromatic C–H Alkenylation with Alkenyl Carbonates

  摘要：

  在催化剂[Ru(cod)(cot)]的存在下，选择性地对芳香C–H进行烯烃化，使用烯烃碳酸酯。芳基吡啶和芳基噁唑啉在不添加外部碱的情况下进行了区域选择性的烯烃化。芳香C–H烷基化也会根据反应条件发生。

  DOI：

  10.1246/cl.140006

文献信息

• Ruthenium-Catalyzed Ortho-Selective C–H Alkenylation of Aromatic Compounds with Alkenyl Esters and Ethers
  作者：Yohei Ogiwara、Masaru Tamura、Takuya Kochi、Yusuke Matsuura、Naoto Chatani、Fumitoshi Kakiuchi

  DOI：10.1021/om401204h

  日期：2014.1.13

  elimination. Two types of catalytically relevant species were identified, and the reactivities of these species, combined with the results of the kinetic studies, suggest that the rate-limiting step is the exchange of the COD ligand with the alkenyl ester. On the basis of the elucidated mechanism, the first catalytic coupling reaction using aromatic C–H bonds with C–O bonds of ethers was also developed

  使用Ru（cod）（cot）作为催化剂，开发了芳基吡啶基和杂芳基吡啶及相关化合物的芳香族C–H键与烯基酯的直接，区域选择性烯基化反应。使带有电子多样性取代基和各种杂环定向基团的芳族化合物与带有带有脂族和芳族取代基的单和二取代烯基的乙酸烯基酯反应，以高收率得到邻烯基化产物。使用不同比例的E和Z进行氘标记实验和竞争反应的结果β-苯乙烯基乙酸酯的异构体表明，C–H烯基化反应是通过钌–烯烃中间体进行的，乙酸烯基酯的C–O键被β-乙酰氧基消除而裂解。确定了两种类型的催化相关物种，这些物种的反应性与动力学研究的结果相结合，表明限速步骤是COD配体与烯基酯的交换。在阐明机理的基础上，还开发了第一个使用芳族C–H键与醚的C–O键的催化偶联反应。
• 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。）
• Efficient Rh(I)-Catalyzed Direct Arylation and Alkenylation of Arene C−H Bonds via Decarbonylation of Benzoic and Cinnamic Anhydrides
  作者：Weiwei Jin、Zhengkun Yu、Wei He、Wenjing Ye、Wen-Jing Xiao

  DOI：10.1021/ol9000729

  日期：2009.3.19

  Efficient rhodium(I)-catalyzed regioselective direct arylation and alkenylation of aromatic C−H bonds has been realized with aromatic carboxylic and cinnamic anhydrides as the coupling partners via decarbonylation and C−H activation under phosphine-free conditions.

  以芳族羧酸和肉桂酸酐为偶合伙伴，通过无羰基条件下的脱羰和CH活化，实现了铑（I）催化的芳族CH键的区域选择性直接芳基化和烯基化反应。
• Method of producing aromatic compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：US08212048B2

  公开（公告）日：2012-07-03

  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 Ar1 ring represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, an Ar2 ring represents a heterocyclic ring containing X1 and N*, and the X1 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 Ar2 ring.) (wherein, R1, R2, R3 and R4 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, Ar1, Ar2, X1, N*, R1, R2 and R3 represent the same meanings as described above.).

  一种制备以下公式（3）的芳香族化合物的方法，包括在过渡金属配合物存在下，将以下公式（1）的化合物与以下公式（2）的烯烃化合物反应：（其中，Ar1环代表芳香族碳氢环或含氮杂环，Ar2环代表含有X1和N*的杂环，X1代表氮原子或碳原子，N代表通过双键连接到Ar2环中两个相邻原子中的任意一个的氮原子。）（其中，R1、R2、R3和R4分别独立地表示氢原子、有1至10个碳原子的烷基或有6至18个碳原子的芳基。）（其中，Ar1、Ar2、X1、N*、R1、R2和R3的含义与上述相同）。
• Rhodium-Catalyzed Direct Alkenylation and Arylation of Arene C−H Bonds via Decarbonylation of Cinnamoyl Chlorides, Cinnamic Anhydrides, and Poly(aroyl) Chlorides
  作者：Wenjing Ye、Ning Luo、Zhengkun Yu

  DOI：10.1021/om900997y

  日期：2010.2.22

  Efficient regioselective direct alkenylation of benzo[h]quinoline was realized with cinnamoyl chlorides as the coupling partners via decarbonylation of the chlorides and C-H bond activation by means of [Rh(CO)(2)Cl](2) as the catalyst in refluxing o-oxlene under phosphine-free conditions. For 2-phenylpridine, [Rh(CO)(2)Cl](2) or [Rh(COD)Cl](2) efficiently promoted its direct alkenylation with cinnamic anhydrides. Polyarenes were synthesized from [Rh(COD)Cl](2)-catalyzed decarbonylative poly(arylation) of isophthaloyl dichloride, terephthaloyl dichloride, or benzene-1,3,5,-tricarbonyl chloride with benzo[h] quinoline.