diethyl 5-methyl-2-(pentafluoroethyl)cyclohexa-1,4-dien-1-ylphosphonate | 1158840-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 5-methyl-2-(pentafluoroethyl)cyclohexa-1,4-dien-1-ylphosphonate
• CAS: 1158840-03-9
• 化学式: C₁₃H₁₈F₅O₃P
• 分子量: 348.25
• InChiKey: DAQAATBNPAESDE-UHFFFAOYSA-N

物化性质

• 沸点：
  81-82 °C(Press: 0.1 Torr)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  diethyl 3,3,4,4,4-pentafluorobut-1-ynylphosphonate 、 天然橡胶 在 对苯二酚 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 diethyl 5-methyl-2-(pentafluoroethyl)cyclohexa-1,4-dien-1-ylphosphonate 、 diethyl 4-methyl-2-(pentafluoroethyl)cyclohexa-1,4-dien-1-ylphosphonate
  参考文献：
  名称：

  Perfluoroacetylenephosphonates in Diels–Alder reactions: Synthesis of perfluoroalkylated heterocyclic and carbocyclic phosphonates

  摘要：

  Diethyl 3,3,3-trifluoroprop-1-ynylphosphonate and diethyl 3,3,4,4,4-pentafluorobut-1-ynylphosphonate are obtained by the dehydration of the corresponding enols using P2O5-Et3N system as a dehydrating agent, affording acetylenes in 50-60% yield. By the reaction of these perfluoroacetylenephosphonates with acyclic and cyclic 1,3-dienes or diene-like heteroaromatic and aromatic compounds corresponding Diels-Alder cyclo- and bicycloadducts were prepared in good yields (65-90%). The reactivity of the dienes and acetylenes which depends on their structure, as well as the regioselectivity of the reaction are established. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.02.009