1-(1H-1,3-imidazol-1-yl)2-phenyl-ethen | 339549-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1H-1,3-imidazol-1-yl)2-phenyl-ethen
• 英文别名: N-styrylimidazole；1-styryl-1H-imidazole；1-Styryl-imidazol；1-(2-Phenylethenyl)imidazole
• CAS: 339549-16-5
• 化学式: C₁₁H₁₀N₂
• 分子量: 170.214
• InChiKey: NSAWYJIGEZYSEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1H-1,3-imidazol-1-yl)2-phenyl-ethen 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 1-methyl-6-phenyl-7,8-dipropylimidazo[1,2-a]pyridin-1-ium trifluoromethanesulfonate
  参考文献：
  名称：

  铑（III）催化的非芳香族sp2 C–H活化/环抱，使用NHC作为导向和可官能团

  摘要：

  In parallel to the directing-group-assisted sp(2) C-H bond: activation functionalization of aromatic backbones, a exercise with nonaromatic Sp(2) C-H bonds is also in high demand in synthetic chemistry, despite several challenges pertinent to the latter process. In; the presented,ptotocol, N-heterocyclic cathene (NHC) motifs, appended to nonaromatic sp(2) C-H bond-containing organic molecules, have been used for developing a rhodium(III)-catalyzed-annulation reaction with, internal alkynes to synthesize a class of ithidazo[1,2-a]pyridiniurn architectures. Mechanistic-studies highlight the directing role of the NHC ligand intermediacy of the C-H-activated Rh-NHC metallacycle in the catalysis.

  DOI：

  10.1021/acs.organomet.6b00530
• 作为产物：
  描述：

  咪唑 、 alpha- 溴苯乙烯 在 potassium phosphate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以80%的产率得到1-(1H-1,3-imidazol-1-yl)2-phenyl-ethen
  参考文献：
  名称：

  磷酸钾促进炔烃向咪唑加成反应的无过渡金属合成N-（1-烯基）咪唑

  摘要：

  据报道，通过在DMSO中与磷酸钾简单地加热，炔烃与N杂环的加成反应。对于一系列底物，可以实现具有高立体选择性的高产率。对于胺和苯乙炔来说，范围是相当普遍的。此外，在此反应中还检查了内部炔烃和α-溴苯乙烯。该方法对于合成（Z）-N-（1-烯基）咪唑和相关的Z 产物是有效的和有用的。因此，由于咪唑支架的重要性，该反应是有用的。

  DOI：

  10.1002/asia.201301173

文献信息

• Nickel catalyzed addition of -NH- containing compounds to vinyl and aryl halides
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP1178040A1

  公开（公告）日：2002-02-06

  A process for producing unsaturated nitrogen containing compounds such as enamides, enamines and aryl amines/amides is disclosed. A vinyl halide or aryl halide is reacted with an -NH- containing compound in the presence of a catalytic amount of a catalyst precursor composition comprising zero-valent nickel and an organophosphine ligand. One step coupling of vinyl halides and aryl halides with -NH- containing compounds is made possible by practice of this invention.

  揭示了一种生产不饱和含氮化合物，如烯酰胺，烯胺和芳基胺/酰胺的方法。在存在催化量的催化剂前体组合物的情况下，将乙烯卤化物或芳基卤化物与含-NH-的化合物反应，所述催化剂前体组合物包括零价镍和有机膦配体。通过实施这一发明，实现了乙烯卤化物和芳基卤化物与含-NH-的化合物的一步偶联。
• An Efficient N-Arylation of Heterocycles with Aryl-, Heteroaryl-, and Vinylboronic Acids Catalyzed by Copper Fluorapatite
  作者：Mannepalli Lakshmi Kantam、Gopaladasu Tirupati Venkanna、Kota Balaji Shiva Kumar、Vura Bala Subrahmanyam

  DOI：10.1002/hlca.200900326

  日期：2010.5

  N‐Arylation of N‐containing heterocycles, such as pyrazoles, imidazoles, and benzimidazoles with aryl‐, heteroaryl‐, and vinylboronic acids was efficiently carried out by copper fluorapatite (CuFAP) catalyst in MeOH at room temperature under base‐free conditions. The N‐arylated heterocycles were isolated in good‐to‐excellent yields.

  Ñ含N杂环，如吡唑，咪唑，并用苯并咪唑的-Arylation芳基- ，杂芳基- ，和vinylboronic酸被有效通过铜氟磷灰石（CuFAP）催化剂在MeOH在室温下游离碱条件下进行的。的N-芳基化的杂环在良好至优异的产率进行分离。
• Maier, Ludwig; Rist, G., Phosphorus and Sulfur and the Related Elements, 1987, vol. 32, p. 65 - 72
  作者：Maier, Ludwig、Rist, G.

  DOI：——

  日期：——
• Transition-Metal-Free Synthesis of<i>N</i>-(1-Alkenyl)imidazoles by Potassium Phosphate-Promoted Addition Reaction of Alkynes to Imidazoles
  作者：Linhua Lu、Hong Yan、Defu Liu、Guangwei Rong、Jincheng Mao

  DOI：10.1002/asia.201301173

  日期：2014.1

  The addition reaction of alkynes to N‐heterocycles by simply heating in DMSO with potassium phosphate is reported. Good yields with high stereoselectivity could be achieved for a range of substrates. The scope is quite general for both amines and phenylacetylenes. In addition, internal alkynes and α‐bromostyrene were also examined in this reaction. This process is efficient and useful for the synthesis

  据报道，通过在DMSO中与磷酸钾简单地加热，炔烃与N杂环的加成反应。对于一系列底物，可以实现具有高立体选择性的高产率。对于胺和苯乙炔来说，范围是相当普遍的。此外，在此反应中还检查了内部炔烃和α-溴苯乙烯。该方法对于合成（Z）-N-（1-烯基）咪唑和相关的Z 产物是有效的和有用的。因此，由于咪唑支架的重要性，该反应是有用的。
• Rhodium(III)-Catalyzed Nonaromatic sp² C–H Activation/Annulation Using NHC as a Directing and Functionalizable Group
  作者：Ranjeesh Thenarukandiyil、Hridya Thrikkykkal、Joyanta Choudhury

  DOI：10.1021/acs.organomet.6b00530

  日期：2016.9.12

  In parallel to the directing-group-assisted sp(2) C-H bond: activation functionalization of aromatic backbones, a exercise with nonaromatic Sp(2) C-H bonds is also in high demand in synthetic chemistry, despite several challenges pertinent to the latter process. In; the presented,ptotocol, N-heterocyclic cathene (NHC) motifs, appended to nonaromatic sp(2) C-H bond-containing organic molecules, have been used for developing a rhodium(III)-catalyzed-annulation reaction with, internal alkynes to synthesize a class of ithidazo[1,2-a]pyridiniurn architectures. Mechanistic-studies highlight the directing role of the NHC ligand intermediacy of the C-H-activated Rh-NHC metallacycle in the catalysis.