1-Fluoro-4-(2-methylene-cyclohexylidene)-adamantane | 136175-88-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-Fluoro-4-(2-methylene-cyclohexylidene)-adamantane
• CAS: 136175-88-7
• 化学式: C₁₇H₂₃F
• 分子量: 246.368
• InChiKey: KYQWQSOOMKWRNP-NXVVXOECSA-N

物化性质

• 沸点：
  329.4±31.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  1-Fluoro-4-(2-methylene-cyclohexylidene)-adamantane 、 四氰基乙烯 以 乙腈 为溶剂， 反应 72.0h， 生成 、
  参考文献：
  名称：

  Face selection in thermal cycloaddition and -reversion

  摘要：

  The isomer distribution has been determined in several cycloaddition reactions involving 5-fluoro- and 5-phenyladamantane derivatives in which C2 serves as one of the trigonal termini. The reactions include a [2 + 2] cycloaddition with dichloroketene, a nucleophilic addition followed by cyclization, a [2 + 2] cycloreversion of a beta-lactone, and two Diels-Alder reactions; in the latter case, the adamantane moiety was incorporated in the diene in one instance and in the dienophile in the other. In all these reactions, the reagent attacking the adamantane substrate was found to do so preferentially at the zu face, by modest but clear margins. This observation is in accord with the concept of transition-state hyperconjugation. This explanation is extended to several literature examples involving substrates with faces that are not isosteric because the polarizing group is placed closer to the site of attack; the ratios are substantial and in favor of the more hindered product in many of these examples.

  DOI：

  10.1021/jo00020a041