2-methyl-4-[4-[(1E)-2-(4-pyridinyl)ethenyl]phenyl]-3-butyn-2-ol | 189190-25-8

• 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: 2-methyl-4-[4-[(1E)-2-(4-pyridinyl)ethenyl]phenyl]-3-butyn-2-ol
• 英文别名: 2-methyl-4-[4-[(E)-2-pyridin-4-ylethenyl]phenyl]but-3-yn-2-ol
• CAS: 189190-25-8
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: QPKHBKDONRWVRG-VMPITWQZSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  431.9±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-4-[4-[(1E)-2-(4-pyridinyl)ethenyl]phenyl]-3-butyn-2-ol 在 吡啶 、 copper(I) chloride 、 sodium hydroxide 、 氧气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成
  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
• 作为产物：
  描述：

  4-碘苄基溴 在 copper(I) chloride 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium tert-butylate 、 二乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 72.5h， 生成 2-methyl-4-[4-[(1E)-2-(4-pyridinyl)ethenyl]phenyl]-3-butyn-2-ol
  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

• Hierarchical Synthesis, Structure, and Photophysical Properties of Gallium‐ and Ruthenium‐Porphyrins with Axially Bonded Azo Ligands
  作者：Yueze Gao、Vroni Walter、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1002/chem.202002030

  日期：2020.12.15

  The hierarchical synthesis of three porphyrin and four bisporphyrin derivatives is presented. This strategy relies on the incorporation of linkers based on azo moieties appended with pyridyl and/or acetylenic groups that facilitate axial coordination to Ga‐ and Ru‐metalloporphyrins. These porphyrinic systems allow for a quantitative analysis of the effects of diamagnetic anisotropy (DA) by using 1H NMR

  介绍了三种卟啉和四种双卟啉衍生物的分级合成。该策略依赖于结合基于偶氮基的连接基，并附加有吡啶基和/或炔属基团，这些基团有利于Ga-和Ru-金属卟啉的轴向配位。这些卟啉系统可通过1 H NMR光谱和X射线晶体学分析对抗磁各向异性（DA）的影响进行定量分析。实验概述了质子化学位移和与卟啉核的距离之间的简单幂律关系，这证实了先前的理论预测，并表明DA的极限约为2 nm。偶氮连接的卟啉的光物理性质通过紫外/可见光谱分析，表明明显的顺式–仅与Ga卟啉结合的偶氮配体未观察到反式异构化。Ru-卟啉与偶氮配体的结合有利于光开关行为，但该过程面临Ru-卟啉脱羰作用的竞争，只有GaL1Ru记录了明显的开关。
• 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.