2-[(Z)-2-(3,4-dimethoxyphenyl)ethenyl]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(Z)-2-(3,4-dimethoxyphenyl)ethenyl]quinoline
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: XAEBIRLRAIYZMN-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(Z)-2-(3,4-dimethoxyphenyl)ethenyl]quinoline 以 乙腈 为溶剂， 生成 (E)-2-(3,4-dimethoxystyryl)quinoline
  参考文献：
  名称：

  Regiospecific C–N Photocyclization of 2-Styrylquinolines

  摘要：

  Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4)2.

  DOI：

  10.1021/jo500696n
• 作为产物：
  描述：

  (E)-2-(3,4-dimethoxystyryl)quinoline 以 乙腈 为溶剂， 生成 2-[(Z)-2-(3,4-dimethoxyphenyl)ethenyl]quinoline
  参考文献：
  名称：

  Regiospecific C–N Photocyclization of 2-Styrylquinolines

  摘要：

  Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4)2.

  DOI：

  10.1021/jo500696n

文献信息

• A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction
  作者：Gaspar Diaz-Muñoz、Raquel Geralda Isidorio、Izabel Luzia Miranda、Gabriel Nunes de Souza Dias、Marisa Alves Nogueira Diaz

  DOI：10.1016/j.tetlet.2017.07.044

  日期：2017.8

  (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

  本研究描述了分三个步骤，高收率合成1,2,3,4-四氢喹啉碱类生物碱（±）-半胱氨酸，（±）-cuspareine，（±）-半乳糖苷和（±）-Angustureine）（78分别从普通醛和叶立德中分离得到1％，76％，74％和66％）。此方法的关键步骤基于使用相转移介质（NaOH / CH 2 Cl 2 1：1水溶液或t -BuOK / t -BuOH / CH 2 Cl 2 1：1水溶液）进行的不寻常的Wittig反应，从而得到烯烃中间体的收率很高。
• Regiospecific C–N Photocyclization of 2-Styrylquinolines
  作者：Elena N. Gulakova、Daria V. Berdnikova、Tseimur M. Aliyeu、Yuri V. Fedorov、Ivan A. Godovikov、Olga A. Fedorova

  DOI：10.1021/jo500696n

  日期：2014.6.20

  Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4)2.