(E)-butyl 3-(5-methylthiophen-2-yl)acrylate | 1041011-44-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-butyl 3-(5-methylthiophen-2-yl)acrylate
• 英文别名: butyl (E)-3-(5-methylthiophen-2-yl)prop-2-enoate
• CAS: 1041011-44-2
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: VTDHWAMWOCQXGM-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基噻吩 、 丙烯酸丁酯 在 3-methyl-2-(phenylthio)butanoic acid 、 silver(I) acetate 、 palladium diacetate 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以88%的产率得到(E)-butyl 3-(5-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

• Sterically controlled C–H alkenylation of pyrroles and thiophenes
  作者：Eunsu Kang、Ju Eun Jeon、Siyeon Jeong、Hyun Tae Kim、Jung Min Joo

  DOI：10.1039/d1cc04378a

  日期：——

  Pd-catalyzed C–H alkenylations targeting the least hindered position of N-alkyl pyrroles and 3-substituted thiophenes, as opposed to electronically controlled approaches, are developed. The steric demand and stable bidentate binding mode of the pyrazolonaphthyridine ligand are key to the success of these sterically controlled alkenylations using oxygen as an oxidant.

  与电子控制方法相反，Pd 催化的 C-H 烯基化靶向N-烷基吡咯和 3-取代噻吩的受阻位置最小。吡唑并萘啶配体的空间需求和稳定的双齿结合模式是这些使用氧作为氧化剂的空间控制烯基化成功的关键。
• Zeolite Y nanosheet assembled palladium catalysts with high catalytic activity and selectivity in the vinylation of thiophenes
  作者：Wenqian Fu、Yu Feng、Zhongxue Fang、Qun Chen、Ting Tang、Quanyong Yu、Tiandi Tang

  DOI：10.1039/c5cc08366d

  日期：——

  Zeolite Y nanosheets with micro-meso-macroporous structure was synthesized, and applied to assemble Pd catalyst (Pd/NS-Y) for direct vinylation of thiophenes in high activity and selectivity, as compared to Pd(OAc)2, Pd(NO3)2,...

  合成了具有介孔结构的Y型沸石纳米片，与Pd（OAc）2，Pd（NO3）相比，具有较高的活性和选择性，可用于组装Pd催化剂（Pd / NS-Y），用于噻吩的直接乙烯基化。 2，...
• Palladium-catalyzed direct oxidative vinylation of thiophenes and furans under weakly basic conditions
  作者：Atsushi Maehara、Tetsuya Satoh、Masahiro Miura

  DOI：10.1016/j.tet.2008.01.058

  日期：2008.6

  The palladium-catalyzed oxidative coupling of thiophenes and furans with alkenes proceeds in the presence of copper and lithium salts as oxidant and additive, respectively, under weakly basic or almost neutral conditions to afford the corresponding vinylated heteroarenes. Under such conditions, diphenyl(hydroxy)methyl and acetal functions on the heteroarene substrates are tolerable. The former function

  在弱碱性或几乎中性的条件下，分别在铜盐和锂盐作为氧化剂和添加剂的情况下，噻吩和呋喃与烯烃的钯催化氧化偶联进行，从而得到相应的乙烯基化杂芳烃。在这样的条件下，杂芳烃底物上的二苯基（羟基）甲基和乙缩醛功能是可以容忍的。噻吩环上的前一个官能团可以在乙烯基化后通过C-C键断裂被钯催化的芳基化反应取代，从而生成2-芳基-5-乙烯基噻吩。
• Palladium-catalyzed alkenation of thiophenes and furans by regioselective C–H bond functionalization
  作者：Jinlong Zhao、Lehao Huang、Kai Cheng、Yuhong Zhang

  DOI：10.1016/j.tetlet.2009.03.124

  日期：2009.6

  A palladium-catalyzed direct alkenation of thiophenes and furans has been developed in the presence of AgOAc and pyridine. A variety of olefinic substrates such as acrylates, acrylamides, and acrylonitrile can perform the direct oxidative coupling reactions with various thiophenes and furans to give the mono-alkenylated products in good yields. In most cases, the (E)-isomers were isolated as the major products. (C) 2009 Elsevier Ltd. All rights reserved.
• 2-Hydroxy-1,10-phenanthroline vs 1,10-Phenanthroline: Significant Ligand Acceleration Effects in the Palladium-Catalyzed Oxidative Heck Reaction of Arenes
  作者：Cheng-Hao Ying、Shao-Bai Yan、Wei-Liang Duan

  DOI：10.1021/ol4033804

  日期：2014.1.17

  A series of bidentate monoanionic nitrogen ligands were designed and applied in the Pd-catalyzed oxidative Heck reaction of arenes with alkenes. Significant ligand-accelerated effects were observed, and direct C-H functionalized products were formed in high yields with meta-selectivity.