4,5-Dimethoxy-2-(2-phenylethenyl)benzaldehyde | 848607-51-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5-Dimethoxy-2-(2-phenylethenyl)benzaldehyde
• 英文别名: 4,5-dimethoxy-2-(2-phenylethenyl)benzaldehyde
• CAS: 848607-51-2
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: YNCALXYTMWPBBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-Dimethoxy-2-(2-phenylethenyl)benzaldehyde 、 环己酮 在 三氟甲磺酸 、 原甲酸三甲酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以69%的产率得到2-(5,6-dimethoxy-2-phenyl-1H-inden-1-yl)cyclohexanone
  参考文献：
  名称：

  In Situ Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from o-Alkenylbenzaldehydes

  摘要：

  A new protocol has been developed for the synthesis of indene derivatives, in a diastereoselective manner from,o-alkenylbenzaldehydes and enolizable ketones hi the presence of trimethyl orthoformate and catalytic triflic acid. This method involves tandem in situ formed acetal-assisted Claisen-Schmidt condensation followed by 5-exo-trig cyclization/Michael addition in one-pot. It has also been shown that the chalcones derived from o-alkenylbenzaldehydes and ketones can effectively be transformed into indene derivatives in the presence of TfOH catalyst alone.

  DOI：

  10.1021/acs.orglett.5b01695
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 硅酸四乙酯 、 tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate 、 copper diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 4,5-Dimethoxy-2-(2-phenylethenyl)benzaldehyde
  参考文献：
  名称：

  Rh(III)-Catalyzed Olefination of N-Sulfonyl Imines: Synthesis of Ortho-Olefinated Benzaldehydes

  摘要：

  Rh(III)-catalyzed olefination of N-sulfonyl imines using acrylates and styrenes has been achieved for the synthesis of ortho-olefinated benaldehydes. This reaction proceeds via a chelation assisted C-H olefination/in situ hydrolysis process.

  DOI：

  10.1021/ol403178a

文献信息

• <i>In Situ</i> Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from <i>o</i>-Alkenylbenzaldehydes
  作者：Seetharaman Manojveer、Rengarajan Balamurugan

  DOI：10.1021/acs.orglett.5b01695

  日期：2015.7.17

  A new protocol has been developed for the synthesis of indene derivatives, in a diastereoselective manner from,o-alkenylbenzaldehydes and enolizable ketones hi the presence of trimethyl orthoformate and catalytic triflic acid. This method involves tandem in situ formed acetal-assisted Claisen-Schmidt condensation followed by 5-exo-trig cyclization/Michael addition in one-pot. It has also been shown that the chalcones derived from o-alkenylbenzaldehydes and ketones can effectively be transformed into indene derivatives in the presence of TfOH catalyst alone.
• Rh(III)-Catalyzed Olefination of <i>N</i>-Sulfonyl Imines: Synthesis of <i>Ortho</i>-Olefinated Benzaldehydes
  作者：Tao Zhang、Lamei Wu、Xingwei Li

  DOI：10.1021/ol403178a

  日期：2013.12.20

  Rh(III)-catalyzed olefination of N-sulfonyl imines using acrylates and styrenes has been achieved for the synthesis of ortho-olefinated benaldehydes. This reaction proceeds via a chelation assisted C-H olefination/in situ hydrolysis process.