(E)-2-(5-methyl-2-styrylphenyl)pyridine

• 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: (E)-2-(5-methyl-2-styrylphenyl)pyridine
• 英文别名: 2-[5-methyl-2-[(E)-2-phenylethenyl]phenyl]pyridine
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: XRHNTLBUIYHVFP-ACCUITESSA-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：

  2-(3-甲苯基)吡啶 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 溶剂黄146 作用下， 以 乙醇 、 氯苯 为溶剂， 反应 66.0h， 生成 (E)-2-(5-methyl-2-styrylphenyl)pyridine
  参考文献：
  名称：

  通过螯合辅助的 C-C 键裂解对烯丙基苯进行直接烯基化

  摘要：

  报道了一种通过铑催化的 CC 键裂解将烯丙基苯衍生物中的烯丙基直接转化为烯基的新方法。含有吡啶基和吡唑基作为导向基团的烯丙基苯与苯乙烯的烯基化反应有效地进行，得到烯基化产物。我们还开发了一种将邻异戊二烯化苯酚转化为苯胺衍生物的新方案。

  DOI：

  10.1021/jacs.8b03718

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。）
• Cobalt(<scp>iii</scp>)-catalyzed alkenylation of arenes and 6-arylpurines with terminal alkynes: efficient access to functional dyes
  作者：Shan Wang、Ji-Ting Hou、Mei-Lin Feng、Xiao-Zhuan Zhang、Shan-Yong Chen、Xiao-Qi Yu

  DOI：10.1039/c5cc09707j

  日期：——

  A method for cobalt(iii)-catalyzed alkenylation of arenes and 6-arylpurines has been developed. This reaction takes place under mild conditions with only equivalent terminal alkynes in high yields. A mitochondria-targeted imaging dye was simply prepared through this method.

  已开发出一种钴（III）催化的芳烃和6-芳基嘌呤的烯烃化方法。该反应在温和条件下进行，仅需等量的末端炔烃即可高产率得到产物。通过这种方法简单制备了一种针对线粒体的成像染料。
• Pyridinyl Directed Alkenylation with Olefins via Rh(III)-Catalyzed C–C Bond Cleavage of Secondary Arylmethanols
  作者：Hu Li、Yang Li、Xi-Sha Zhang、Kang Chen、Xin Wang、Zhang-Jie Shi

  DOI：10.1021/ja205228y

  日期：2011.10.5

  Novel C-C bond cleavage of secondary alcohols through Rh(III)-catalyzed β-carbon elimination directed by a pyridinyl group is reported. A five-membered rhodacycle is proposed as a key intermediate, which undergoes further alkenylation with various olefins. This novel transformation shows high efficiency along with excellent selectivity in mild conditions. A wide range of functionalities are compatible

  报道了仲醇通过由吡啶基团引导的 Rh(III) 催化的 β-碳消除来裂解仲醇的新型 CC 键。五元罗达环被提议作为关键中间体，它与各种烯烃进行进一步的烯基化。这种新型转化在温和条件下显示出高效率和出色的选择性。兼容多种功能。本研究提供了一种新的策略来进行 CC 键活化。
• Rhodium-Catalyzed Decarbonylative Direct Olefination of Arenes with Vinyl Carboxylic Acids
  作者：Ruiying Qiu、Lingjuan Zhang、Conghui Xu、Yixiao Pan、Hongze Pang、Lijin Xu、Huanrong Li

  DOI：10.1002/adsc.201401020

  日期：2015.4.13

  A rhodium(I)‐catalyzed direct CH bond olefination of pyridyl‐substituted arenes with readily available vinyl carboxylic acids has been realized. This reaction occurred efficiently without the need for any external oxidant, affording the ortho‐olefinated products in high yields and excellent regioselectivities. Diversely substituted vinyl carboxylic acids behaved as efficient olefination reagents under

  吡啶取代的芳烃与易于获得的乙烯基羧酸的铑（I）催化的直接CH键烯化反应已实现。该反应无需任何外部氧化剂即可有效地进行，从而以高收率和出色的区域选择性提供了正构烯烃产品。在反应条件下，不同取代的乙烯基羧酸可作为有效的烯化试剂，并且两个偶联配偶体中的一系列官能团均具有良好的耐受性。机理研究表明，该催化过程涉及脱羰步骤，新戊酸酐[（t- BuCO）2 O]充当原位羧酸的活化剂。 生成高活性酸酐。
• The Ru(cod)(cot)-Catalyzed Alkenylation of Aromatic C−H Bonds with Alkenyl Acetates
  作者：Yusuke Matsuura、Masaru Tamura、Takuya Kochi、Mitsuo Sato、Naoto Chatani、Fumitoshi Kakiuchi

  DOI：10.1021/ja071965m

  日期：2007.8.1

  The regioselective Ru(cod)(cot)-catalyzed alkenylation of arylpyridines and related compounds with alkenyl acetates to give good-to-excellent yields of ortho-alkenylation products was developed. Several arylpyridines having electron-donating (CH3 and OCH3) and -withdrawing (CF3, CN, and Ac) groups and azoles, such as oxazoline, tetrazole, and thiazole, can be used in this coupling reaction. A variety of alkenyl acetates, such as 1-propenyl, 1-butenyl, 1-hexenyl, styryl, 2-methyl-1-propenyl, and 1-cyclohexenyl acetates, reacted with arylpyridines to give the corresponding ortho-alkenylation products in high yields. This direct alkenylation of aromatic C-H bonds with alkenyl acetates provides pi-conjugated aromatic and heteroaromatic compounds under halogen-free reaction conditions.