p-chloro-4'-stilbazole | 46459-15-8

• 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: p-chloro-4'-stilbazole
• 英文别名: Pyridine, 4-[(1E)-2-(4-chlorophenyl)ethenyl]-；4-[2-(4-chlorophenyl)ethenyl]pyridine
• CAS: 46459-15-8
• 化学式: C₁₃H₁₀ClN
• 分子量: 215.682
• InChiKey: PONMZBJRRLHVPF-UHFFFAOYSA-N

物化性质

• 沸点：
  346.7±11.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-chloro-4'-stilbazole 在 溴 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 (4-氯苯基)(4-吡啶基)乙炔
  参考文献：
  名称：

  Photo-dehydro-Diels–Alder reaction of 1-phenyl-2-(pyridyl)acetylenes in acidic aqueous solution

  摘要：

  The photocycloaddition of 1-(4-R-phenyl)-2-(4-pyridyl)acetylenes (R = H, Br, CH3, Cl) and 1-(4-R-phenyl)-2-(2-pyridyl)acetylenes (R = H, Br, Cl) was carried out in acidic aqueous solution. The unexpected photo-dehydro-Diels-Alder reaction of these monomers was observed, and the results show that two monomers react in a head-to-tail manner and lead to the formation of 2-phenyl-1,3-di(pyridyl)naphthalene derivatives. This reaction presents a direct metal-free method to construct the 1,2,3-triaryl substituted naphthalenes from diarylacetylenes. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.07.004
• 作为产物：
  描述：

  4-吡啶甲醛 、 (4-chlorobenzyl)triphenylphosphonium bromide 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 生成 p-chloro-4'-stilbazole
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9

文献信息

• Facile and highly selective silylation of vinylpyridines at the β-olefinic carbon by magnesium-promoted reduction
  作者：Tianyuan Zhang、Zeyu Zhang、Yutaro Nishiyama、Hirofumi Maekawa

  DOI：10.1016/j.tet.2016.03.042

  日期：2016.5

  Magnesium-promoted reductive silylation of 2- and 4-vinylpyridines with chlorotrialkylsilanes in N-methylpyrrolidinone at room temperature led to the selective formation of a variety of the corresponding β-mono-silylated compounds at the terminal carbon atom in good to excellent yields, whereas silylation of 3-vinylpyridine under the same reduction conditions failed to give a complex mixture of silylated

  在室温下，镁在N-甲基吡咯烷酮中用氯三烷基硅烷促进2-和4-乙烯基吡啶的还原甲硅烷基化，从而导致在末端碳原子上选择性形成各种相应的β-单甲硅烷基化化合物，而收率很好，反而更好。在相同的还原条件下使3-乙烯基吡啶甲硅烷基化不能得到甲硅烷基化化合物的复杂混合物。2-或4-乙烯基吡啶与3-乙烯基吡啶之间的结果差异归因于通过与吡啶的氮原子的共振对反应中间体的稳定作用。
• [2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension
  作者：Thanh Binh Nguyen、Tuan Minh Nguyen、Pascal Retailleau

  DOI：10.1002/chem.201905597

  日期：2020.4.9

  waxy or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to sub-stoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additive to improve or even overturn regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than

  在这项研究中，我们报道了一种非常简单的技术，可以有效地对某些乙烯基吡啶进行光二聚化。通过用几种苯乙烯基唑与分散在非极性（例如环己烷）或中等极性（苯，二氯甲烷，二恶烷）溶剂中的固体草酸二水合物的搅拌混合物进行辐照，可以高收率获得相应的二聚环丁烷加合物，具有极好的区域选择性。和立体选择性。该策略也可以成功地应用于油性，蜡质或什至不溶性斯蒂巴唑。此外，草酸负载量可降低至亚化学计量量。当需要进一步优化时，我们的策略非常灵活，可以确定其他低聚羧酸作为替代添加剂，从而改善甚至推翻区域选择性。
• Comparison of Templating Abilities of Urea and Thioruea During Photodimerization of Bipyridylethyelene and Stilbazole Crystals
  作者：Balakrishna R. Bhogala、Burjor Captain、Vaidhyanathan Ramamurthy

  DOI：10.1111/php.12353

  日期：2015.5

  AbstractPhotodimerization of cocrystals of four bispyridylethylenes and two stilbazoles with urea as a template in the solid state has been investigated following our success with thiourea. Four investigated olefins photodimerized quantitatively to a single dimer in the crystalline state only. The reactivity of urea–olefin crystals is understood on the basis of their packing arrangements in the crystalline state. In reactive crystals the adjacent reactive molecules are within 4.2 Å and parallel, whereas the unreactive ones have their adjacent molecules are farther than 4.6Å and nonparallel. Thus, with the knowledge of crystal packing the reactivity of urea–olefin crystals is predictable on the basis of Schmidt's topochemical postulates. The templating property of urea, similar to thiourea, derives from its ability to form hydrogen bonds with itself and the guest olefins. Despite the similarities in molecular structures of urea and thiourea their subtle electronic properties, yet to be fully understood, affect the crystal packing and consequently their reactivity in the crystalline state. Further work is needed to fully exploit the templating properties of urea.
• Selective introduction of a trifluoroacetyl group onto 4-vinylpyridines through magnesium-promoted reduction
  作者：Hirofumi Maekawa、Yutaro Nishiyama

  DOI：10.1016/j.tet.2015.07.046

  日期：2015.9

  Magnesium-promoted reductive coupling of 4-vinylpyridines and ethyl trifluoroacetate in the presence of chlorotrimethylsilane in N-methyl-2-pyrrolidone resulted in selective formation of the tri-fluoroacetylated compounds at the beta-olefinic carbon of the pyridine ring, the electron deficient carbon in good yields. In particular, 4-vinylpyridine with an aromatic ring at the beta-olefinic position of the pyridine ring gave higher yield of the trifluoroacetylated compound. The nitrogen atom of the pyridine ring may play an important role in the regioselectivity of the product. (C) 2015 Elsevier Ltd. All rights reserved.
• π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes
  作者：J.Gonzalo Rodrı́guez、Rosa Martı́n-Villamil、Antonio Lafuente

  DOI：10.1016/s0040-4020(02)01628-9

  日期：2003.2

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.