(1E,4E)-2,4-dimethyl-1,5-diphenyl-3-(phenylethynyl)penta-1,4-dien-3-ol | 1258392-42-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (1E,4E)-2,4-dimethyl-1,5-diphenyl-3-(phenylethynyl)penta-1,4-dien-3-ol
• 英文别名: (1E,4E)-2,4-dimethyl-1,5-diphenyl-3-(2-phenylethynyl)penta-1,4-dien-3-ol
• CAS: 1258392-42-5
• 化学式: C₂₇H₂₄O
• 分子量: 364.487
• InChiKey: ALDPIWDYUJMSPV-DQPVQCHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 (1E,4E)-2,4-dimethyl-1,5-diphenyl-3-(phenylethynyl)penta-1,4-dien-3-ol 在 2,3,4,5-四氟苯硼酸 作用下， 以 硝基甲烷 为溶剂， 反应 16.0h， 以87%的产率得到
  参考文献：
  名称：

  Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition

  摘要：

  Boronic acid catalysis (BAC) was applied to a sequential Nazarov cyclization of divinyl alcohols/Diels-Alder cycloadditions leading to the preparation of highly functionalized bicyclic compounds in a highly diastereoselective fashion. In these one-pot transformations, highly functionalized dienes were generated in situ through boronic acid catalyzed Nazarov cyclizations of divinyl alcohols and were subsequently trapped with different dienophiles such as maleic anhydride and phenylmaleimide. The tandem reactions proceed directly from divinyl alcohols under very mild reaction conditions using air-stable catalysts, and as such this methodology represents a greener alternative to existing methods employing strong Lewis and Bronsted acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.100
• 作为产物：
  描述：

  1,5-二苯基-2,4-二甲基-1,4-戊二烯-3-酮 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 以95%的产率得到(1E,4E)-2,4-dimethyl-1,5-diphenyl-3-(phenylethynyl)penta-1,4-dien-3-ol
  参考文献：
  名称：

  Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition

  摘要：

  Boronic acid catalysis (BAC) was applied to a sequential Nazarov cyclization of divinyl alcohols/Diels-Alder cycloadditions leading to the preparation of highly functionalized bicyclic compounds in a highly diastereoselective fashion. In these one-pot transformations, highly functionalized dienes were generated in situ through boronic acid catalyzed Nazarov cyclizations of divinyl alcohols and were subsequently trapped with different dienophiles such as maleic anhydride and phenylmaleimide. The tandem reactions proceed directly from divinyl alcohols under very mild reaction conditions using air-stable catalysts, and as such this methodology represents a greener alternative to existing methods employing strong Lewis and Bronsted acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.100

文献信息

• Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition
  作者：Hongchao Zheng、Michal Lejkowski、Dennis G. Hall

  DOI：10.1016/j.tetlet.2012.10.100

  日期：2013.1

  Boronic acid catalysis (BAC) was applied to a sequential Nazarov cyclization of divinyl alcohols/Diels-Alder cycloadditions leading to the preparation of highly functionalized bicyclic compounds in a highly diastereoselective fashion. In these one-pot transformations, highly functionalized dienes were generated in situ through boronic acid catalyzed Nazarov cyclizations of divinyl alcohols and were subsequently trapped with different dienophiles such as maleic anhydride and phenylmaleimide. The tandem reactions proceed directly from divinyl alcohols under very mild reaction conditions using air-stable catalysts, and as such this methodology represents a greener alternative to existing methods employing strong Lewis and Bronsted acids. (C) 2012 Elsevier Ltd. All rights reserved.