(E)-4-ethoxy-4-(4-nitrostyryl)benzene | 67644-10-4

• 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: (E)-4-ethoxy-4-(4-nitrostyryl)benzene
• 英文别名: ethyl-(4'-nitro-trans-stilben-4-yl)-ether；Aethyl-(4'-nitro-trans-stilben-4-yl)-aether；Benzene, 1-ethoxy-4-[2-(4-nitrophenyl)ethenyl]-, (E)-；1-[(E)-2-(4-ethoxyphenyl)ethenyl]-4-nitrobenzene
• CAS: 67644-10-4
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: OMQWWRBNFWPIRR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙氧基苯乙烯 、 4-nitrobenzenediazonium tetrafluoroborate 在 9-甲基氨基-萘嵌苯-1-酮 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以65%的产率得到(E)-4-ethoxy-4-(4-nitrostyryl)benzene
  参考文献：
  名称：

  Transition-Metal-Free Catalytic Carboalkoxylation of Styrenes at Room Temperature

  摘要：

  Herein, we describe the first transition-metal-free catalytic carboalkoxylation of styrenes with aryl diazonium salts by Meerwein addition in the presence of a phenalenyl ligand at room temperature without requiring any light stimulation. This three-component reaction allows facile difunctionalization of styrene derivatives with various alcohols (such as 1, 2, and 3 degrees) as the source of alkoxy group during this transformation. The key intermediates and the transition states involved in this reaction path were unraveled by a series of control experiments coupled with density functional theory calculations. The full mechanistic investigation provides an understanding of the selectivity toward carboalkoxylation Meerwein arylation addition elimination) in the presence of various alcohols over the simple arylation to multiple bond (Meerwein arylation-elimination) reaction.

  DOI：

  10.1021/acs.joc.9b01744

文献信息

• Runti; Bucher, Annali di Chimica, 1957, vol. 47, p. 356,360
  作者：Runti、Bucher

  DOI：——

  日期：——
• DUBOIS J.-C.; ZANN A.; HUU TINH NGUYEN, C. R. ACAD. SCI., 1977, C 284, NO 3, 137-139
  作者：DUBOIS J.-C.、 ZANN A.、 HUU TINH NGUYEN

  DOI：——

  日期：——
• Transition-Metal-Free Catalytic Carboalkoxylation of Styrenes at Room Temperature
  作者：R. Govindarajan、Jasimuddin Ahmed、Asim Kumar Swain、Swadhin K. Mandal

  DOI：10.1021/acs.joc.9b01744

  日期：2019.11.1

  Herein, we describe the first transition-metal-free catalytic carboalkoxylation of styrenes with aryl diazonium salts by Meerwein addition in the presence of a phenalenyl ligand at room temperature without requiring any light stimulation. This three-component reaction allows facile difunctionalization of styrene derivatives with various alcohols (such as 1, 2, and 3 degrees) as the source of alkoxy group during this transformation. The key intermediates and the transition states involved in this reaction path were unraveled by a series of control experiments coupled with density functional theory calculations. The full mechanistic investigation provides an understanding of the selectivity toward carboalkoxylation Meerwein arylation addition elimination) in the presence of various alcohols over the simple arylation to multiple bond (Meerwein arylation-elimination) reaction.