ethyl 5-(2-phenylethynyl)thiophene-2-carboxylate | 1362419-60-0

• 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: ethyl 5-(2-phenylethynyl)thiophene-2-carboxylate
• CAS: 1362419-60-0
• 化学式: C₁₅H₁₂O₂S
• 分子量: 256.325
• InChiKey: XOKDZMURPFQPFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-噻吩羧酸乙酯 、 苯乙炔 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 三乙胺 、 silver(l) oxide 、 三甲基乙酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 10.0h， 以75%的产率得到ethyl 5-(2-phenylethynyl)thiophene-2-carboxylate
  参考文献：
  名称：

  低催化剂负载下杂环与末端炔烃之间的钯催化氧化交叉偶联

  摘要：

  直接：以[Pd 2（dba）3 ]为催化剂，通过使用末端炔烃作为炔基化试剂，可实现带有多种取代基的噻吩的直接炔基化。该协议也适用于其他富电子芳族杂环。dba ＝二亚苄基丙酮。

  DOI：

  10.1002/anie.201210013

文献信息

• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.
• Palladium-Catalyzed Oxidative Cross-Coupling between Heterocycles and Terminal Alkynes with Low Catalyst Loading
  作者：Xiaoming Jie、Yaping Shang、Peng Hu、Weiping Su

  DOI：10.1002/anie.201210013

  日期：2013.3.25

  Direct: With [Pd2(dba)3] as a catalyst, the direct alkynylation of thiophenes bearing a variety of substituents has been accomplished by using terminal alkynes as alkynylating reagents. This protocol is also applicable to other electron‐rich aromatic heterocycles. dba=dibenzylidenacetone.

  直接：以[Pd 2（dba）3 ]为催化剂，通过使用末端炔烃作为炔基化试剂，可实现带有多种取代基的噻吩的直接炔基化。该协议也适用于其他富电子芳族杂环。dba ＝二亚苄基丙酮。