1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-2-methoxypropane | 150771-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-2-methoxypropane
• 英文别名: 1-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-2-iodobenzene
• CAS: 150771-61-2
• 化学式: C₁₀H₇F₆IO
• 分子量: 384.06
• InChiKey: OPFVGKFRVMUYFH-UHFFFAOYSA-N

物化性质

• 熔点：
  32-33.5 °C(Solv: hexane (110-54-3))
• 沸点：
  249.3±40.0 °C(Predicted)
• 密度：
  1.767±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-2-methoxypropane 、 3,3-bis(trifluoromethyl)-1-chloro-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole 在 BuLi 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以29.7%的产率得到1,1-bis(p-methylphenyl)-1-(2-(2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl)phenyl)-3,3-bis(trifluoromethyl)-3H-2,1λ5-benzoxabismole
  参考文献：
  名称：

  具有双齿配体（12-Bi-6）的六配位有机铋化合物的合成与结构

  摘要：

  The thermally stable 12-Bi-6 compound 3-Li+, {(o-C6H4C(CF3)20)2}Bi(p-CH3C6H4)2-Li+, was synthesized. F-19 NMR of 3-Li+ showed a pair of quartets at room temperature but showed a singlet after addition of 12-crown-4 to the solution. The result indicated an important role of the Li+ on the structure of the ate complex, and the structure of the Li salt was assigned as 3A, bearing two cis oxygens, two cis p-tolyl groups, and two trans carbons at ligation sites about the central bismuth atom. The structure of the ate complex in the presence of 12-crown-4 was assigned as 3C, bearing two cis oxygens, two trans p-tolyl groups, and two cis carbons at ligation sites. Compounds 3 were stable up to 150-degrees-C, but the pair of quartets coalesced at 70-degrees-C and the activation energy of the equilibrium between the CF3 groups was calculated to be 18 kcal mol-1 at 70-degrees-C. Bismuth-oxygen bond cleavage followed by pseudorotation was suggested for the coalescence. Compounds 3 were inert to electrophilic reagents such as p-(trifluoromethyl) benzoyl chloride. Water reacted with 3 to give an alcohol 17. The alcohol was unstable at room temperature and cyclized with elimination of toluene to afford a 10-Bi-5 (12). Intramolecularly coordinated 12-Bi-6 compounds 18, (o-C6H4C(CF3)20)BiAr2(o-C6H4CR2X) { Ar, R, X: 18a p-CH3C6H4, CF3, CH3O; 18b p-CF3C6H4, CF3, CH3O; 18c p-CH3C6H4, H, (CH3)2N; 18d p-CF3C6H4, H, (CH3)2N}, were synthesized, three of which were structurally determined by X-ray analysis. The structures were all cis geometry. The synthesis and stability of 12-Bi-6 ate complexes 5, (o-C6H4C(CF3)20)Bi(P-CH3C6H4)3R-Li+, were also described.

  DOI：

  10.1021/om00032a060
• 作为产物：
  描述：

  1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)propan-2-ol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以29%的产率得到1,1,1,3,3,3-hexafluoro-2-(2-iodophenyl)-2-methoxypropane
  参考文献：
  名称：

  烷基自由基从芳香族碘化物中提取碘：立体效应和电子效应† ，‡

  摘要：

  尽管烷基和芳基碘化物中C-1键的键解离能存在不利差异，但烷基基团从芳基碘化物中碘原子的提取非常有效。在碘代苯中，用大基团邻位取代是最有效的方法。抽象的难易程度可以通过消除碘原子过程中释放空间应变来解释。通过密度泛函理论（DFT）和Hartree-Fock（HF）方法计算出的抽象速率与应变能相当相关，这是邻位异构体和对位异构体的总能量之差。但是，除了空间体积外，邻位取代基中某些其他官能团的存在也会影响该速率。过渡态的稳定化，类似于9-I-2碘基自由基，

  DOI：

  10.1021/jo061125a