diethyl 2-cyclopropyl-2-phenylethene-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl 2-cyclopropyl-2-phenylethene-1,1-dicarboxylate
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: BFQDCXMIEUFMAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯基锂 、 diethyl 2-cyclopropyl-2-phenylethene-1,1-dicarboxylate 以 乙醚 、 环己烷 为溶剂， 以38%的产率得到1-cyclopropyl-1-phenyl-2,2-bis(diphenylhydroxymethyl)ethene
  参考文献：
  名称：

  (Hexaphenyltrimethylene)methane Dication and Related Carbocations

  摘要：

  By ionization of the respective alkenediol (8a), the (hexaphenyltrimethylene)methane dication (2) has been prepared and found stable in solution under superacidic stable ion conditions (FSO3H/SO2ClF) up to at least -20 degrees C. The spectroscopic data and AM1 theoretical modeling indicate that although the entire pi-system is twisted, phenyl groups stabilize the positive charges in 2 to a similar degree as those in the trityl cation. The hexa-p-CF3 derivative of 2 was also observable but only at very low temperatures (-90 degrees C). Disruption of the 3-fold symmetry and reduction of the number of stabilizing phenyl rings even to five resulted in intramolecular allylation and subsequent formation of the corresponding indenyl cations. In all the cases studied no evidence for ''Y-aromatic'' stabilization was found.

  DOI：

  10.1021/ja00150a017
• 作为产物：
  描述：

  苯基环丙基甲酮 、 丙二酸二乙酯 在 吡啶 、 四氯化钛 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 96.0h， 以17%的产率得到diethyl 2-cyclopropyl-2-phenylethene-1,1-dicarboxylate
  参考文献：
  名称：

  (Hexaphenyltrimethylene)methane Dication and Related Carbocations

  摘要：

  By ionization of the respective alkenediol (8a), the (hexaphenyltrimethylene)methane dication (2) has been prepared and found stable in solution under superacidic stable ion conditions (FSO3H/SO2ClF) up to at least -20 degrees C. The spectroscopic data and AM1 theoretical modeling indicate that although the entire pi-system is twisted, phenyl groups stabilize the positive charges in 2 to a similar degree as those in the trityl cation. The hexa-p-CF3 derivative of 2 was also observable but only at very low temperatures (-90 degrees C). Disruption of the 3-fold symmetry and reduction of the number of stabilizing phenyl rings even to five resulted in intramolecular allylation and subsequent formation of the corresponding indenyl cations. In all the cases studied no evidence for ''Y-aromatic'' stabilization was found.

  DOI：

  10.1021/ja00150a017

文献信息

• (Hexaphenyltrimethylene)methane Dication and Related Carbocations
  作者：Nicholas J. Head、George A. Olah、G. K. Surya Prakash

  DOI：10.1021/ja00150a017

  日期：1995.11

  By ionization of the respective alkenediol (8a), the (hexaphenyltrimethylene)methane dication (2) has been prepared and found stable in solution under superacidic stable ion conditions (FSO3H/SO2ClF) up to at least -20 degrees C. The spectroscopic data and AM1 theoretical modeling indicate that although the entire pi-system is twisted, phenyl groups stabilize the positive charges in 2 to a similar degree as those in the trityl cation. The hexa-p-CF3 derivative of 2 was also observable but only at very low temperatures (-90 degrees C). Disruption of the 3-fold symmetry and reduction of the number of stabilizing phenyl rings even to five resulted in intramolecular allylation and subsequent formation of the corresponding indenyl cations. In all the cases studied no evidence for ''Y-aromatic'' stabilization was found.