ethyl 2-(7-oxo-9-phenyl-1,6-dioxaspiro[4.4]non-8-en-4-ylidene)acetate | 1198272-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(7-oxo-9-phenyl-1,6-dioxaspiro[4.4]non-8-en-4-ylidene)acetate
• CAS: 1198272-14-8
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: MJULPVVDDXHQGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙醛酸乙酯 、 1-环丙基-2-苯乙酮 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68%的产率得到4-Phenyl-1,6-dioxaspiro[4.4]non-3-en-2-one
  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

文献信息

• Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with diethyl 2-oxomalonate and ethyl 2-oxoacetate
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1016/j.tet.2009.09.003

  日期：2009.11

  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.