n-butyl 3-[5-(2-n-butoxycarbonylvinyl)-3-methylthiophen-2-yl]acrylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: n-butyl 3-[5-(2-n-butoxycarbonylvinyl)-3-methylthiophen-2-yl]acrylate
• 英文别名: dibutyl 3,3'-(3-methylthiophene-2,5-diyl)(2E,2'E)-diacrylate；butyl (E)-3-[5-[(E)-3-butoxy-3-oxoprop-1-enyl]-4-methylthiophen-2-yl]prop-2-enoate
• 化学式: C₁₉H₂₆O₄S
• 分子量: 350.479
• InChiKey: XVJMKIPVDRDQIZ-GFULKKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲基噻吩 、 丙烯酸丁酯 在 碘苯二乙酸 、 3-methyl-2-(phenylthio)butanoic acid 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以26%的产率得到n-butyl 3-(3-methylthiophen-2-yl)acrylate
  参考文献：
  名称：

  S,O-配体促进的 Pd 催化的噻吩的 CH 烯烃化

  摘要：

  这么好。已经使用易于获得的双齿 S,O-配体开发了一种有效的 PdII 催化的噻吩的 C-H 烯化。该催化体系在温和条件下促进包括 3-取代噻吩在内的多种噻吩中的 C-2 烯化。

  DOI：

  10.1002/ejoc.201900077

文献信息

• Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates
  作者：Andrew G. Myers、Daisuke Tanaka、Michael R. Mannion

  DOI：10.1021/ja027523m

  日期：2002.9.1

  The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described. The optimized procedure for decarboxylative palladation employs Pd(O2CCF3)2 as catalyst (0.2 equiv) in the presence of Ag2CO3 (3 equiv) in the solvent 5% DMSO-DMF and proceeds at temperatures of 80-120 degrees C with a wide range of arene carboxylates and alkenes as substrates. The process is proposed to proceed by an initial Ar-SE reaction involving ipso attack of an electrophilic Pd(II) intermediate on an arene carboxylate to form an arylpalladium(II) species with loss of carbon dioxide. This intermediate is then proposed to react with an olefinic substrate by steps common to the Heck coupling process. Reoxidation of the liberated Pd(0) in situ is proposed to establish the catalytic cycle.
• S,O-Ligand-Promoted Pd-Catalyzed C-H Olefination of Thiophenes
  作者：Yolanda Álvarez-Casao、M. Ángeles Fernández-Ibáñez

  DOI：10.1002/ejoc.201900077

  日期：2019.2.28

  SO good. An efficient PdII catalyzed C−H olefination of thiophenes has been developed using an easily accessible bidentate S,O‐ligand. The catalytic system promotes the C‐2 olefination in a wide range of thiophenes including 3‐substituted thiophenes, under mild conditions.

  这么好。已经使用易于获得的双齿 S,O-配体开发了一种有效的 PdII 催化的噻吩的 C-H 烯化。该催化体系在温和条件下促进包括 3-取代噻吩在内的多种噻吩中的 C-2 烯化。