3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane
• 英文别名: Cyclobutane, 1,1,2,2-tetrafluoro-3-cyclopropyl-
• 化学式: C₇H₈F₄
• 分子量: 168.134
• InChiKey: XRFSFWSPEYDSIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙烯基-1,1,2,2-四氟环丁烷 以 乙醚 为溶剂， 反应 73.0h， 生成 3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane
  参考文献：
  名称：

  摘要：

  The reactions of diazomethane and diazocyclopropane generated in situ with 1,1,2,2-tetrafluoro-3-vinylcyclobutane (1) and 2,3,3-trifluoro-1-vinylcyclobutene (2) proceeded at the double bond of the substituent as the 1,3-dipolar cycloaddition to form the corresponding 1-pyrazolines. Under the conditions of thermolysis (340-400 degreesC), the resulting cyclobutylpyrazolines 4 and 5 selectively lost the dinitrogen molecule to generate 3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane (6) or 1,1, 2,2-tetrafluoro-3-spiropentylcyclobutane (7), respectively, in high yields. In the presence of Pd(acac)(2), the reactions of these fluorine-containing unsaturated compounds and 2-chloro-1,1,2-trifluoro-3-vinylcyclobutane (3) with diazomethane gave rise directly to cyclopropane derivatives 6, 11, and 12, respectively. The reactions of compounds 1 and 2 with methyl diazoacetate in the presence of Rh-2(OAc)(4) proceeded analogously to yield cis- and trans-disubstituted cyclopropanes.

  DOI：

  10.1023/a:1015049317831

文献信息

• ——
  作者：Yu. V. Tomilov、E. V. Guseva、N. V. Volchkov、E. V. Shulishov

  DOI：10.1023/a:1015049317831

  日期：——

  The reactions of diazomethane and diazocyclopropane generated in situ with 1,1,2,2-tetrafluoro-3-vinylcyclobutane (1) and 2,3,3-trifluoro-1-vinylcyclobutene (2) proceeded at the double bond of the substituent as the 1,3-dipolar cycloaddition to form the corresponding 1-pyrazolines. Under the conditions of thermolysis (340-400 degreesC), the resulting cyclobutylpyrazolines 4 and 5 selectively lost the dinitrogen molecule to generate 3-cyclopropyl-1,1,2,2-tetrafluorocyclobutane (6) or 1,1, 2,2-tetrafluoro-3-spiropentylcyclobutane (7), respectively, in high yields. In the presence of Pd(acac)(2), the reactions of these fluorine-containing unsaturated compounds and 2-chloro-1,1,2-trifluoro-3-vinylcyclobutane (3) with diazomethane gave rise directly to cyclopropane derivatives 6, 11, and 12, respectively. The reactions of compounds 1 and 2 with methyl diazoacetate in the presence of Rh-2(OAc)(4) proceeded analogously to yield cis- and trans-disubstituted cyclopropanes.