4-(2-chloro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester | 1206896-65-2

• 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-(2-chloro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester
• 英文别名: ethyl 4-(2-chlorophenyl)-2-methyl-2,3-butadienoate
• CAS: 1206896-65-2
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: MVBHCGJJQGVNMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 9.0h， 生成 2-(1-phenyl-1H-indol-2-yl)propionic acid
  参考文献：
  名称：

  Palladium-Catalyzed Tandem Allenyl and Aryl C–N Bond Formation: Efficient Access to N-Functionalized Multisubstituted Indoles

  摘要：

  An efficient palladium-catalyzed synthesis of N-functionalized multisubstituted indoles from easily accessible ortho-haloarylallenes and primary amines has been developed. A wide range of electronically and structurally varied nitrogen fragments could be introduced through this tandem C-N bond-forming process by tuning the reaction conditions.

  DOI：

  10.1021/ol3018775
• 作为产物：
  描述：

  邻氯苯乙酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 4-(2-chloro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Tandem Allenyl and Aryl C–N Bond Formation: Efficient Access to N-Functionalized Multisubstituted Indoles

  摘要：

  An efficient palladium-catalyzed synthesis of N-functionalized multisubstituted indoles from easily accessible ortho-haloarylallenes and primary amines has been developed. A wide range of electronically and structurally varied nitrogen fragments could be introduced through this tandem C-N bond-forming process by tuning the reaction conditions.

  DOI：

  10.1021/ol3018775

文献信息

• Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor™: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates
  作者：Bo Lü、Chunling Fu、Shengming Ma

  DOI：10.1039/b917793k

  日期：——

  Different from the reaction of 2,3-allenoic acids with Selectfluor™, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor™ under different conditions in moderate yields. The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed.

  与2,3-烯酸与Selectfluor™反应不同，在不同条件下，2,4-取代的2,3-烯酸酯与Selectfluor™反应，能够高选择性地生成4-氟-2(5H)-呋喃酮和(E)-3-氟-4-氧代-2-烯酸酯，产率适中。2,4,4-三取代的2,3-烯酸酯的反应在不同条件下高选择性地生成相应的4-氟-2(5H)-呋喃酮，产率高达95%。对底物的范围进行了仔细探讨。由于与2,3-烯酸相比，2,3-烯酸酯更易获得，因此合成了新的4-氟-2(5H)-呋喃酮。基于小量氟羟基化产物E-5m的分离和表征，提出了一种机制。