methyl 1-phenylthio-2-chloro-2,3,3-trifluorocyclobutane carboxylate | 139008-27-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 1-phenylthio-2-chloro-2,3,3-trifluorocyclobutane carboxylate
• 英文别名: Methyl 2-chloro-2,3,3-trifluoro-1-phenylsulfanylcyclobutane-1-carboxylate
• CAS: 139008-27-8
• 化学式: C₁₂H₁₀ClF₃O₂S
• 分子量: 310.724
• InChiKey: VXALPRLGZBDJAI-UHFFFAOYSA-N

物化性质

• 沸点：
  343.1±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  三氟氯乙烯 、 methyl 2-(phenylthio)propenoate 反应 8.0h， 以80%的产率得到methyl 1-phenylthio-2-chloro-2,3,3-trifluorocyclobutane carboxylate
  参考文献：
  名称：

  Activation of acrylate-moiety by strain and fluoroalkyl substitution in 4-chloro-3,3,4-trifluoro-methoxycarbonyl cyclobutene

  摘要：

  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.

  DOI：

  10.1016/0040-4039(91)80494-q