3-(methoxycarbonyl)-5-methyl-5-phenyl-γ-butyrolactone | 52267-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(methoxycarbonyl)-5-methyl-5-phenyl-γ-butyrolactone
• 英文别名: Methyl 5-methyl-2-oxo-5-phenyloxolane-3-carboxylate
• CAS: 52267-49-9
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: AHXCQDMOMHGSIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  monomethyl monopotassium malonate 、 2-苯基-1-丙烯 在 ammonium cerium(IV) nitrate 、 copper diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以51%的产率得到3-(methoxycarbonyl)-5-methyl-5-phenyl-γ-butyrolactone
  参考文献：
  名称：

  硝酸铈铵和丙二酸单甲酯对烯烃的声化学内酯化

  摘要：

  在简单的机械搅拌或超声辐射下，在乙酸和乙腈中，用丙二酸和硝酸硝酸铈铵的单甲酯对烯烃进行酯化。报告了比较结果；对于活性烯烃，观察到良好的超声加速。

  DOI：

  10.1016/s0040-4039(00)73056-5

文献信息

• Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes
  作者：Enrico Baciocchi、Renzo Ruzziconi

  DOI：10.1021/jo00015a037

  日期：1991.7

  The addition reactions of 1,3-dicarbonylalkyl radicals to ring-substituted styrenes have been kinetically investigated in MeOH and/or MeCN. It has been observed that the rate effect of ring substituents is nearly identical in the reactions of MeCOCHCOMe (1), MeOCOCHCOMe (2) and MeOCOCHCOOMe (4), the rho-value, in MeOH being -0.96, -1.01 and -1.06, respectively. Since the three radicals are relatively strong oxidants and have similar reduction potentials, an important contribution of the charge transfer structure RCOCHCORCH2CHAr.+ to the addition transition state is suggested. It has also be found that in the reactions of 1 and 4 with alpha-alkyl-substituted styrenes the rate of addition is strongly influenced by the nature of the alkyl group, decreasing in the order: Me > Et > (i)Pr > (t)Bu. The observed effects are much larger than those reported for the corresponding reactions of the nucleophilic cyclohexyl radical. It is suggested that the alpha-alkyl substituents exert an effect of steric inhibition of resonance thereby ring delocalization of the charge and/or unpaired electron in the transition state is significantly reduced. Delocalization may be more important in the reactions of 1 and 4 than in those of the cyclohexyl radical since it is possible that the former utilizes a transition state occurring later along the reaction coordinate and/or characterized by a larger extent of charge transfer.