1-methylene-3-fluorocyclobutane | 143902-19-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-methylene-3-fluorocyclobutane
• 英文别名: 1-Fluoro-3-methylidenecyclobutane
• CAS: 143902-19-6
• 化学式: C₅H₇F
• 分子量: 86.109
• InChiKey: QHNSLXGNBJPVBB-UHFFFAOYSA-N

物化性质

• 沸点：
  52.8±9.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [1.1.1]螺桨烷 在 二氟代氙 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以64%的产率得到1-methylene-3-fluorocyclobutane
  参考文献：
  名称：

  Nucleophilic substitution in 1-substituted 3-iodobicyclo[1.1.1]pentanes. A new synthetic route to functionalized bicyclo[1.1.1]pentane derivatives

  摘要：

  Nucleophilic substitution of the iodine in 1-substituted 3-iodobicyclo[1.1.1]pentanes [R = I (1), CF3 (2)] was investigated. The results of the reaction are strongly dependent on the nature of the nucleophile and the substituent. Whereas the trifluoromethyl derivative 2 is found to be inert in the reactions and gave substitution products only with organolithium reagents, the 1,3-diiodide 1 is much more reactive and affords normal substitution products with nitrogen bases and MeONa but gives [1.1.1]propellane with Grignard and organolithium reagents and with triaryl(alkyl)phosphines. Other synthesized 3-iodobicyclo[1.1.1]pentanes did not give substitution products. A general scheme for the transformations of 1 is also proposed.

  DOI：

  10.1021/jo00049a030

文献信息

• Facile Synthesis of Methylenecyclobutyl-Related Compounds via Rearrangement­ of Methylenecyclopropylcarbinols in the Presence of Multifluorosulfonyl­ Fluorides and Base
  作者：Li-Xiong Shao、Min Shi、Ming-Hui Qi

  DOI：10.1055/s-2007-990836

  日期：2007.11

  Methylenecyclopropylcarbinols treated with multifluorosulfonyl fluorides and triethylamine form the 3-methylenecyclobutyl fluorides and 3-methylenecyclobutyl (2-methylenecyclo­-propyl)methyl ethers in good to high total yields. A proposed mechanism is based on the obtained results.

  亚甲基环丙基甲醇经多氟磺酰氟和三乙胺处理后生成 3-亚甲基环丁基氟化物和 3-亚甲基环丁基（2-亚甲基环丙基）甲基醚，总产率从好到高。根据获得的结果提出了一种机理。
• Nucleophilic substitution in 1-substituted 3-iodobicyclo[1.1.1]pentanes. A new synthetic route to functionalized bicyclo[1.1.1]pentane derivatives
  作者：James L. Adcock、Andrei A. Gakh

  DOI：10.1021/jo00049a030

  日期：1992.11

  Nucleophilic substitution of the iodine in 1-substituted 3-iodobicyclo[1.1.1]pentanes [R = I (1), CF3 (2)] was investigated. The results of the reaction are strongly dependent on the nature of the nucleophile and the substituent. Whereas the trifluoromethyl derivative 2 is found to be inert in the reactions and gave substitution products only with organolithium reagents, the 1,3-diiodide 1 is much more reactive and affords normal substitution products with nitrogen bases and MeONa but gives [1.1.1]propellane with Grignard and organolithium reagents and with triaryl(alkyl)phosphines. Other synthesized 3-iodobicyclo[1.1.1]pentanes did not give substitution products. A general scheme for the transformations of 1 is also proposed.