(E)-1-(4-methoxy-2-pyridyl)-2-phenylethene

• 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: (E)-1-(4-methoxy-2-pyridyl)-2-phenylethene
• 英文别名: 4-methoxy-2-[(E)-2-phenylethenyl]pyridine
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: ILZQVFGYKFPQKI-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (3,5-bis(trifluoromethyl)phenyl)glycine 、 (E)-1-(4-methoxy-2-pyridyl)-2-phenylethene 在 disodium hydrogenphosphate 、 蒽 、 DPZ 、 C₄₉H₃₁O₄P 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以50%的产率得到(S)-N-(3-(4-methoxypyridin-2-yl)-2-phenylpropyl)-3,5-bis(trifluoromethyl)aniline
  参考文献：
  名称：

  通过协同光氧化还原和手性氢键催化对烯基氮杂芳烃进行不对称氢化氨基烷基化

  摘要：

  烯基氮杂芳烃的高度对映选择性加氢氨基烷基化被描述为首次成功地将自由基催化不对称共轭加成到活化的烯烃上，从而在其 β 位直接形成立体中心。通过引入协同的非经典氢键相互作用使立体选择性转化成为可能，从而使手性催化剂能够提供足够的立体控制。

  DOI：

  10.1002/anie.202115110
• 作为产物：
  描述：

  4-甲氧基吡啶 、 苯基乙炔基三甲基硅烷 在 sodium hexaflorophosphate 、 二(三苯基膦)环戊二烯基氯化钌(II) 作用下， 反应 11.0h， 以74%的产率得到(E)-1-(4-methoxy-2-pyridyl)-2-phenylethene
  参考文献：
  名称：

  Ruthenium-Mediated Regio- and Stereoselective Alkenylation of Pyridine

  摘要：

  A novel alkenylation reaction of pyridine is developed. Heating a cationic ruthenium vinylidene complex [CpRu(=C=CHR)(PPh(3))(2)]PF(6) in pyridine at 100-125 degrees C for 24 h affords (E)-2-alkenylpyridine. Initially, pyridine coordinates to ruthenium by displacement of one of the phosphine ligands. Then, [2 + 2] heterocycloaddition occurs to form a four-membered ruthenacyclic complex. Deprotonation of the beta-hydrogen affords a neutral pi-azaallyl complex. Protonolysis furnishes the product. As a result, a vinylidene group is inserted into the alpha C-H bond of pyridine. The alkenylation reaction is made catalytic in ruthenium by the use of (alkyn-1-yl)silane as the vinylidene source. Treatment of (alkyn-1-yl)trimethylsilane with pyridine in the presence of a cationic ruthenium complex [CpRu(PPh(3))(2)]PF(6) affords the corresponding (E)-2-alkenylpyridine in good yield in a regio- and stereoselective manner.

  DOI：

  10.1021/ja029829z

文献信息

• Solid Phase Synthesis of 1,2-Disubstituted Alkenes: A Novel Alkynyldihydropyridine to Alkenylpyridine Isomerization
  作者：Chixu Chen、Bowei Wang、Benito Munoz

  DOI：10.1055/s-2003-43343

  日期：——

  A series of 1,2-disubstituted pyridylalkenes have been prepared using a solid-phase resin approach. This approach takes advantage of a novel alkynyldihydropyridine to alkenylpyridine isomerization.

  采用固相树脂法合成了一系列1,2-二取代吡啶基烯烃，该方法利用了新型炔基二氢吡啶向烯基吡啶的异构化反应。
• Ruthenium-Mediated Regio- and Stereoselective Alkenylation of Pyridine
  作者：Masahiro Murakami、Seiji Hori

  DOI：10.1021/ja029829z

  日期：2003.4.1

  A novel alkenylation reaction of pyridine is developed. Heating a cationic ruthenium vinylidene complex [CpRu(=C=CHR)(PPh(3))(2)]PF(6) in pyridine at 100-125 degrees C for 24 h affords (E)-2-alkenylpyridine. Initially, pyridine coordinates to ruthenium by displacement of one of the phosphine ligands. Then, [2 + 2] heterocycloaddition occurs to form a four-membered ruthenacyclic complex. Deprotonation of the beta-hydrogen affords a neutral pi-azaallyl complex. Protonolysis furnishes the product. As a result, a vinylidene group is inserted into the alpha C-H bond of pyridine. The alkenylation reaction is made catalytic in ruthenium by the use of (alkyn-1-yl)silane as the vinylidene source. Treatment of (alkyn-1-yl)trimethylsilane with pyridine in the presence of a cationic ruthenium complex [CpRu(PPh(3))(2)]PF(6) affords the corresponding (E)-2-alkenylpyridine in good yield in a regio- and stereoselective manner.
• Asymmetric Hydroaminoalkylation of Alkenylazaarenes via Cooperative Photoredox and Chiral Hydrogen‐Bonding Catalysis
  作者：Xiangpei Chai、Xinheng Hu、Xiaowei Zhao、Yanli Yin、Shanshan Cao、Zhiyong Jiang

  DOI：10.1002/anie.202115110

  日期：2022.3

  addition of radicals to activated olefins to directly forge stereocenters at their β-position. The stereoselective transformation was made possible by the introduction of cooperative nonclassical H-bonding interactions, thus enabling the chiral catalyst to provide sufficient stereocontrol.

  烯基氮杂芳烃的高度对映选择性加氢氨基烷基化被描述为首次成功地将自由基催化不对称共轭加成到活化的烯烃上，从而在其 β 位直接形成立体中心。通过引入协同的非经典氢键相互作用使立体选择性转化成为可能，从而使手性催化剂能够提供足够的立体控制。