1-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)adamantane | 76500-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)adamantane
• CAS: 76500-90-8
• 化学式: C₁₃H₁₆F₆O
• 分子量: 302.26
• InChiKey: XFEZNBWHCCCOOY-UHFFFAOYSA-N

物化性质

• 沸点：
  252.5±35.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)adamantane 以16%的产率得到
  参考文献：
  名称：

  ALLARD B.; CASADEVALL A.; CASADEVALL E.; LARGEAU C., NOUV. J. CHIM., 1980, 4, NO 8-9, 539-545

  摘要：

  DOI：
• 作为产物：
  描述：

  2-adamantyl hexafluoropropan-2-yl ether 以43%的产率得到
  参考文献：
  名称：

  ALLARD B.; CASADEVALL A.; CASADEVALL E.; LARGEAU C., NOUV. J. CHIM., 1980, 4, NO 8-9, 539-545

  摘要：

  DOI：

文献信息

• Solvolysis-decomposition ofN-1-adamantyl-N-p-tolylcarbamoyl chloride in hydroxylic solvents
  作者：Dennis N. Kevill、Veena Upadhyay

  DOI：10.1002/(sici)1099-1395(199708)10:8<600::aid-poc928>3.0.co;2-q

  日期：1997.8

  In hydroxylic solvents, N-1-adamantyl-N-p-tolylcarbamoyl chloride undergoes a facile rate-determing ionization with very little assistance from nucleophilic solvation (very low sensitivity to changes in solvent nucleophillcity). In the relatively nucleophilic aqueous ethanol or aqueous acetone, the cation formed reacts directly with the solvent. In fluoroalcohols, the low nucleophilicity of the solvent allows an effective competition from a pathway involving disproportionation to the 1-adamantyl cation and p-tolyl isocyanate, followed by reaction of the new cation either with solvent or with the chloride ion formed in the initial ionization, Grunwald-Winstein plots against Y-Cl values show for different binary solvent systems a marked dispersion, which can be considerably reduced by incorporation into the analyses of a term governed by the aromatic ring parameter. (I). (C) 1997 by John Wiley & Sons, Ltd.
• Multiple pathways in the solvolysis of 1-adamantyl fluoroformate
  作者：Dennis N. Kevill、Jin Burm Kyong

  DOI：10.1021/jo00027a046

  日期：1992.1

  Reactions of 1-adamantyl fluoroformate in hydroxylic solvents have been studied. In solvents of high ionizing power and relatively low nucleophilicity, such as 2,2,2-trifluoroethanol-water mixtures, the reactions parallel those of 1-adamantyl chloroformate, and only solvolysis-decomposition reaction is observed. However, differing from the reactions of the corresponding chloroformate, in other solvents appreciable amounts of attack at acyl carbon occur, more than 90% in greater-than-or-equal-to 80% aqueous ethanol. Entropies of activation for attack at acyl carbon are considerably more negative than for solvolysis-decomposition. For the solvolysis-decomposition, a Grunwald-Winstein m value of 0.70 is observed. The k(Cl)/k(F) ratios for solvolysis-decomposition are in the range of 10(4)-10(5), suggesting appreciable C-X bond breaking in the transition state of the rate-determining step and arguing against rate-determining formation of a 1-Ad+(OCOX)-ion pair. Attack at acyl carbon is analyzed in terms of the two-term Grunwald-Winstein equation, and sensitivities toward changes in nucleophilicity and ionizing power are identical to those for solvolyses of n-octyl fluoroformate, which are believed to proceed via a tetrahedral intermediate. For each of the major pathways, selectivities toward the components of binary hydroxylic solvents are reported and discussed.