2,2,3-trifluoro-4,5-bis(trifluoromethyl)-6-phenyl-2H-pyran | 1206484-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,2,3-trifluoro-4,5-bis(trifluoromethyl)-6-phenyl-2H-pyran
• 英文别名: 2,2,3-Trifluoro-6-phenyl-4,5-bis(trifluoromethyl)pyran
• CAS: 1206484-46-9
• 化学式: C₁₃H₅F₉O
• 分子量: 348.168
• InChiKey: ZTUCQWQFSWCHRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  溴代三氟代乙烯 、 苯甲酰氯 、 六氟-2-丁炔 在 锌 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以76%的产率得到2,2,3-trifluoro-4,5-bis(trifluoromethyl)-6-phenyl-2H-pyran
  参考文献：
  名称：

  The synthesis of fluorinated α-pyrans via fluorinated vinylcopper reagents

  摘要：

  Fluorinated vinylcopper reagents were prepared in situ via reaction of fluorinated vinylbromides or iodides with cadmium or zinc powder followed by metathesis with Cu(I)Br. Hexafluoro-2-butyne was then added to the solution of the F-vinylcopper reagent which resulted in a stereospecific syn addition of the F-vinylcopper reagent to the alkyne to provide in situ the corresponding dienylcopper reagent. Subsequent acylation of the dienylcopper reagent gave a dienylketone, which spontaneously cyclized to the 2H-pyran. This methodology provides a useful one flask route to fluorinated 2H-pyrans. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.05.007

文献信息

• The synthesis of fluorinated α-pyrans via fluorinated vinylcopper reagents
  作者：Donald J. Burton、Steven W. Hansen

  DOI：10.1016/j.jfluchem.2009.05.007

  日期：2009.9

  Fluorinated vinylcopper reagents were prepared in situ via reaction of fluorinated vinylbromides or iodides with cadmium or zinc powder followed by metathesis with Cu(I)Br. Hexafluoro-2-butyne was then added to the solution of the F-vinylcopper reagent which resulted in a stereospecific syn addition of the F-vinylcopper reagent to the alkyne to provide in situ the corresponding dienylcopper reagent. Subsequent acylation of the dienylcopper reagent gave a dienylketone, which spontaneously cyclized to the 2H-pyran. This methodology provides a useful one flask route to fluorinated 2H-pyrans. (C) 2009 Elsevier B.V. All rights reserved.