4-(2,5-dimethoxyphenyl)-but-1-yne | 305347-43-7

• 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: 4-(2,5-dimethoxyphenyl)-but-1-yne
• 英文别名: 2-(but-3-ynyl)-1,4-dimethoxybenzene；2-But-3-ynyl-1,4-dimethoxybenzene
• CAS: 305347-43-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: LFPULSUUXOGARE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2,5-dimethoxyphenyl)-but-1-yne 在 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 以34%的产率得到1,8-bis(2,5-dimethoxyphenyl)-octa-3,5-diyne
  参考文献：
  名称：

  Synthesis, X-Ray Structure Analysis and Topochemical Photopolymerization of 2,5-Dimethoxyphenyl- and Quinone-substituted Octa-3,5-diynes

  摘要：

  The octa-3,5-diynes 3a-g have been synthesized. Subsequent oxidation of 3a-g gave the 1,8-quinone-substituted octa-3,5-diynes 4a-g. The molecular structures of the diynes alpha-3b, beta-3b, 3c, 3e, 3f and 4f have been determined by X-ray diffraction. UV-irradiation of diyne 3e afforded in a single crystal-to-single crystal transformation the highly-ordered polymer 5 under topochemical control. The transformation of 3c into polymer 5 was observed by X-ray diffraction analysis. Irradiation of 4d yielded the first quinone-substituted intensive-blue poly(but-1-en-3-ynylene) 5, which turned red after work up. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00500-7
• 作为产物：
  描述：

  1-(2,5-dimethoxyphenyl)but-3-yn-1-ol 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以59%的产率得到4-(2,5-dimethoxyphenyl)-but-1-yne
  参考文献：
  名称：

  Superoxide mediated isomerization of 4-aryl-but-1-ynes to 1-aryl-1,3-butadienes

  摘要：

  A new role of superoxide ion in the isomerization of homobenzylic acetylenes leading to 1-aryl-1,3-butadienes is reported. The unconventional reagent 1(02 is found to be superior in performing this kind of isomerization over other the commonly used bases. For substrates containing arene moiety and triple bond connected through more than two methylene groups, and for propargylcyclohexanol the reagent selectively effected migration of the triple bond. Reactivity of 1(02 towards the substrates having disubstitution at benzylic position varied depending on the nature of the substitution, alkyl-substitution lead to isomerization to give mixture of allene (an intermediate in the isomerization of acetylene to 1,3-butadiene) and triple bond migration product; whereas phenyl-substituted compound gave 1,3-diene. The utility of the methodology was demonstrated through a Diels-Alder reaction of one of the dienes obtained by the isomerization with suitable dienophiles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.075

文献信息

• Superoxide mediated isomerization of 4-aryl-but-1-ynes to 1-aryl-1,3-butadienes
  作者：Faiz Ahmed Khan、Basavaraj M. Budanur

  DOI：10.1016/j.tet.2015.07.075

  日期：2015.10

  A new role of superoxide ion in the isomerization of homobenzylic acetylenes leading to 1-aryl-1,3-butadienes is reported. The unconventional reagent 1(02 is found to be superior in performing this kind of isomerization over other the commonly used bases. For substrates containing arene moiety and triple bond connected through more than two methylene groups, and for propargylcyclohexanol the reagent selectively effected migration of the triple bond. Reactivity of 1(02 towards the substrates having disubstitution at benzylic position varied depending on the nature of the substitution, alkyl-substitution lead to isomerization to give mixture of allene (an intermediate in the isomerization of acetylene to 1,3-butadiene) and triple bond migration product; whereas phenyl-substituted compound gave 1,3-diene. The utility of the methodology was demonstrated through a Diels-Alder reaction of one of the dienes obtained by the isomerization with suitable dienophiles. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, X-Ray Structure Analysis and Topochemical Photopolymerization of 2,5-Dimethoxyphenyl- and Quinone-substituted Octa-3,5-diynes
  作者：Hermann Irngartinger、Markus Skipinski

  DOI：10.1016/s0040-4020(00)00500-7

  日期：2000.9

  The octa-3,5-diynes 3a-g have been synthesized. Subsequent oxidation of 3a-g gave the 1,8-quinone-substituted octa-3,5-diynes 4a-g. The molecular structures of the diynes alpha-3b, beta-3b, 3c, 3e, 3f and 4f have been determined by X-ray diffraction. UV-irradiation of diyne 3e afforded in a single crystal-to-single crystal transformation the highly-ordered polymer 5 under topochemical control. The transformation of 3c into polymer 5 was observed by X-ray diffraction analysis. Irradiation of 4d yielded the first quinone-substituted intensive-blue poly(but-1-en-3-ynylene) 5, which turned red after work up. (C) 2000 Elsevier Science Ltd. All rights reserved.