4-(1-thiophenyl)-1-furoic acid ethyl ester | 1191446-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 4-(1-thiophenyl)-1-furoic acid ethyl ester
• 英文别名: ethyl 5-(thiophen-2-yl)furan-2-carboxylate
• CAS: 1191446-28-2
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: RBSVOONLCRYSSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  ethyl 1-phenoxy-2-(thiophene-2-carbonyl)cyclopropanecarboxylate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到4-(1-thiophenyl)-1-furoic acid ethyl ester
  参考文献：
  名称：

  Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor–Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates

  摘要：

  A direct synthetic strategy starting from alkyl 1-alkoxy-2-aroylcyclopropanecarboxylates was developed for the construction of alkyl 5-arylfuran-2-carboxylates. These donor acceptor cyclopropanes smoothly undergo a simple ring opening reaction or/and cycloisomerization reaction in the presence of acid at room temperature;, which greatly depends on the properties of the acid used in the experiment, Alkyl 5-arylfuran-2-carboxylates were afforded in high yields in triflic acid, whereas alkyl 2,5-dioxo-5-phenylpentanoate became the major product in other protic acids and Lewis acids.

  DOI：

  10.1021/acs.joc.6b00161

文献信息

• Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant
  作者：Gérard Cahiez、Christophe Duplais、Julien Buendia

  DOI：10.1002/anie.200902188

  日期：2009.8.24

  Oxidative heterocoupling between two Grignard reagents RMgX and R′MgX is made possible by manganese catalysis with O2 as an oxidant. This procedure, development of which was based on mechanistic analysis of the corresponding homocoupling reaction, can be steered towards the heterocoupling product at the expense of the homocoupling products by judicious choice of the R and R′ groups (see examples).

  通过以O 2为氧化剂的锰催化，可以实现两种格氏试剂RMgX和R'MgX之间的氧化杂化。该方法的开发是基于对相应的均偶联反应的机理分析，可以通过明智地选择R和R'基团，以牺牲均偶联产物为导向，转向异偶联产物（参见示例）。