4-chloro-3,3,4-trifluoro-1-methoxycarbonylcyclobutene | 2613-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-chloro-3,3,4-trifluoro-1-methoxycarbonylcyclobutene
• 英文别名: 4-chloro-3,3,4-trifluoro-methoxycarbonyl cyclobutene；1-Methoxycarbonyl-3.3.4-trifluor-4-chlor-cyclobuten；Methyl 4-chloro-3,3,4-trifluorocyclobutene-1-carboxylate
• CAS: 2613-47-0
• 化学式: C₆H₄ClF₃O₂
• 分子量: 200.545
• InChiKey: ROGWARQNNATTQP-UHFFFAOYSA-N

物化性质

• 沸点：
  145.1±40.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-3,3,4-trifluoro-1-methoxycarbonylcyclobutene 550.0 ℃ 、266.64 Pa 条件下， 生成 1,4,4-Trifluor-1-chlor-2-methoxycarbonyl-butadien
  参考文献：
  名称：

  Fluorodienes. I. Synthesis from Cyclobutenes

  摘要：

  DOI：

  10.1021/ja01463a030
• 作为产物：
  描述：

  methyl 1-phenylthio-2-chloro-2,3,3-trifluorocyclobutane carboxylate 在 间氯过氧苯甲酸 作用下， 以 苯 为溶剂， 以90%的产率得到4-chloro-3,3,4-trifluoro-1-methoxycarbonylcyclobutene
  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

文献信息

• Synthesis and reactivity of 4-chloro-3,3,4-trifluoro-methoxycarbonyl cyclobutene (CTMC)
  作者：Marie-Aim�e Plancquaert、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1002/prac.19943360106

  日期：——

  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.
• Fluorobutadienecarboxylic acids and derivatives hydrolyzable thereto
  申请人：DU PONT

  公开号：US02754323A1

  公开（公告）日：1956-07-10