4-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic acid methyl ester | 952527-22-9

• 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: 4-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic acid methyl ester
• 英文别名: methyl 4-(1-methoxy-4-methyl-1-oxopenta-2,3-dien-2-yl)benzoate
• CAS: 952527-22-9
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: FLYJTZVNLSBOFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic 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85%的产率得到4-[4-isopropenyl-1-(4-nitro-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-benzoic 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
• 作为产物：
  描述：

  对溴苯甲酸甲酯 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 67.5h， 生成 4-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic 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

• A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
  作者：Guobi Chai、Shangze Wu、Chunling Fu、Shengming Ma

  DOI：10.1021/ja1108694

  日期：2011.3.23

  polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically

  描述了一种合成多取代环丁烯酮的有效方法，由于固有的环应变，这些方法不易从传统方法中获得。2,3-烯丙酸酯和有机锌试剂的反应通过串联迈克尔加成/环状 1,2-加成/消除机制进行，来自有机锌试剂的官能团被区域特异性地引入环丁烯酮产物的 3-位优良的产量。演示了在立体定义的 β,γ-不饱和烯酮的合成中的应用。
• 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.