2-(3-(dimethylcarbamoyl)phenyl)-4-methyl-penta-2,3-dienoic acid methyl ester | 952527-19-4

• 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: 2-(3-(dimethylcarbamoyl)phenyl)-4-methyl-penta-2,3-dienoic acid methyl ester
• CAS: 952527-19-4
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: GMCGCOUTDPHZOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-(dimethylcarbamoyl)phenyl)-4-methyl-penta-2,3-dienoic acid methyl ester 、 1-异氰基-4-硝基苯 在 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以76%的产率得到3-[4-isopropenyl-1-(4-nitro-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethyl-benzamide
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086
• 作为产物：
  描述：

  3-溴-N,N-二甲基苯甲酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 35.5h， 生成 2-(3-(dimethylcarbamoyl)phenyl)-4-methyl-penta-2,3-dienoic acid methyl ester
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086

文献信息

• Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters
  作者：Yuanzhen Li、Haixia Zou、Jianxian Gong、Jing Xiang、Tuoping Luo、Junmin Quan、Guoxin Wang、Zhen Yang

  DOI：10.1021/ol7018086

  日期：2007.9.1

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.