methyl 3,3-difluoro-2,2,4-tris(ethylthio)-cyclobutane carboxylate | 139008-40-5

• 分子结构分类: 有机化合物
• 英文名称: methyl 3,3-difluoro-2,2,4-tris(ethylthio)-cyclobutane carboxylate
• 英文别名: methyl 2,2,4-tris(ethylsulfanyl)-3,3-difluorocyclobutane-1-carboxylate
• CAS: 139008-40-5
• 化学式: C₁₂H₂₀F₂O₂S₃
• 分子量: 330.484
• InChiKey: GPYZBZWCRXQBIR-UHFFFAOYSA-N

物化性质

• 沸点：
  398.6±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl 1-phenylthio-2-chloro-2,3,3-trifluorocyclobutane carboxylate 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 methyl 3,3-difluoro-2,2,4-tris(ethylthio)-cyclobutane carboxylate
  参考文献：
  名称：

  Synthesis and reactivity of 4-chloro-3,3,4-trifluoro-methoxycarbonyl cyclobutene (CTMC)

  摘要：

  An improved synthesis of CTMC is described. This cyclobutene is thermally stable towards electrocyclic ring opening. Its reactivity is explored and a number of radical adducts are described. A more complicated picture is observed with various nucleophiles. The strong dienophilic character of CTMC is illustrated by numerous examples. CTMC reacts well as a dipolarophile with diphenylnitrone, diphenylnitrilimine and diazoalkanes. The high reactivity of this cyclobutene is due to its inherent polarity and strain.

  DOI：

  10.1002/prac.19943360106

文献信息

• Activation of acrylate-moiety by strain and fluoroalkyl substitution in 4-chloro-3,3,4-trifluoro-methoxycarbonyl cyclobutene
  作者：Marie-Aimée Plancquaert、Philippe François、Robert Merényi、Heinz G. Viehe

  DOI：10.1016/0040-4039(91)80494-q

  日期：1991.12

  A two step preparation is reported for the title cyclobutene derivative 3 starting from 2-phenylthioacrylate 1 and chlorotrifluoroethylene followed by oxidative elimination. Strain and polarity facilitate reactions with nucleophiles, radicals, dienes and diazoalkanes.