| 1198272-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• CAS: 1198272-26-2
• 化学式: C₁₇H₁₅FO₅
• 分子量: 318.302
• InChiKey: NHLFOUHYLJVVEI-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  环丙基3-氟苄基甲酮 、 乙醛酸乙酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以59%的产率得到
  参考文献：
  名称：

  Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with diethyl 2-oxomalonate and ethyl 2-oxoacetate

  摘要：

  TMSOTf-mediated reactions of 2-aryl-1-(1-phenylcyclopropyl)ethanones 1 with diethyl 2-oxomalonate 2 afford a novel method for the synthesis of spiro-gamma-lactone derivatives 3 in good to excellent yields via a sequential reaction involving a nucleophilic ring-opening reaction of the cyclopropane by H2O, an aldol-type reaction and a cyclic transesterification mediated by Lewis acid. On the other hand, we found that TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones 1 with ethyl 2-oxoacetate 4 could also provide the corresponding spiro-gamma-lactone derivatives 5 in moderate yields along with another spiro-gamma-lactone derivatives 6 derived from the reaction of 1 with two molecules of ethyl 2-oxcracetate. The plausible reaction mechanisms have also been provided on the basis of control experiments. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.003