tetramethyl 5-phenylfuran-2,2,3,4(5H)-tetracarboxylate | 82545-25-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetramethyl 5-phenylfuran-2,2,3,4(5H)-tetracarboxylate
• 英文别名: tetramethyl 2-phenyl-2H-furan-3,4,5,5-tetracarboxylate
• CAS: 82545-25-3
• 化学式: C₁₈H₁₈O₉
• 分子量: 378.336
• InChiKey: XOZXAHPWMOGVDM-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  448.1±45.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-叠氮丙二酸二甲酯 、 苯甲醛 、 丁炔二酸二甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以41%的产率得到tetramethyl 5-phenylfuran-2,2,3,4(5H)-tetracarboxylate
  参考文献：
  名称：

  A practical system to synthesize the multiple-substituted 2,5-dihydrofuran by the intermolecular dipolar cycloaddition reactions involving acceptor/acceptor-substituted diazo reagents

  摘要：

  A practical system for synthesizing the multiple-substituted 2,5-dihydrofuran through intermolecular dipolar cycloaddition reactions of acceptor/acceptor diazo reagents, aldehydes, and acetylenedicarboxylate was developed. The reactions proceeded effectively under ambient temperature with low reactant ratios. The control reactions revealed that there are two competitive paths: one forms 1,3-dioxolane and the other forms 2,5-dihydrofuran. These two paths could be controlled by modifying the steric hindrance of the diazo reagents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.028

文献信息

• HUISGEN, R.;MARCH, P., J. AMER. CHEM. SOC., 1982, 104, N 18, 4953-4954
  作者：HUISGEN, R.、MARCH, P.

  DOI：——

  日期：——
• A practical system to synthesize the multiple-substituted 2,5-dihydrofuran by the intermolecular dipolar cycloaddition reactions involving acceptor/acceptor-substituted diazo reagents
  作者：Shifa Zhu、Lijuan Chen、Chao Wang、Renxiao Liang、Xiujun Wang、Yanwei Ren、Huanfeng Jiang

  DOI：10.1016/j.tet.2011.05.028

  日期：2011.7

  A practical system for synthesizing the multiple-substituted 2,5-dihydrofuran through intermolecular dipolar cycloaddition reactions of acceptor/acceptor diazo reagents, aldehydes, and acetylenedicarboxylate was developed. The reactions proceeded effectively under ambient temperature with low reactant ratios. The control reactions revealed that there are two competitive paths: one forms 1,3-dioxolane and the other forms 2,5-dihydrofuran. These two paths could be controlled by modifying the steric hindrance of the diazo reagents. (C) 2011 Elsevier Ltd. All rights reserved.