2,2,3,3,3-pentafluoro-1-(naphthalen-1-yl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,3,3,3-pentafluoro-1-(naphthalen-1-yl)propan-1-ol
• 英文别名: 1-(1-Naphthyl)-2,2,3,3,3-pentafluoro-1-propanol；2,2,3,3,3-pentafluoro-1-naphthalen-1-ylpropan-1-ol
• 化学式: C₁₃H₉F₅O
• 分子量: 276.206
• InChiKey: BSGNTVRTYGWWLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(2,2,3,3,3-pentafluoropropanoyl)piperidine 、 1-萘甲醛 在 三乙基氢硼化钾 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到2,2,3,3,3-pentafluoro-1-(naphthalen-1-yl)propan-1-ol
  参考文献：
  名称：

  Polyfluoroalkylation of Carbonyl Compounds by Polyfluoroalkyl Anions Generated from Polyfluorcarboxamides

  摘要：

  Polyfluoroalkyl anions, generated by reduction of (polyfluoroalkanoyl)piperidines with Et3BHK, were used for the polyfluoroalkylation of carbonyl compounds. Trifluoromethylation of aromatic aldehydes proceeded in good yields, and that of aliphatic aldehydes afforded a moderate yield. In contrast, the yield was low when the reaction involved benzophenone. Pentafluoroethylation and octafluorobutylation of aldehydes were also carried out by using the corresponding (polyfluoroalkanoyl)piperidines, which were prepared from commercially available polyfluorocompounds. The (polyfluoroalkanoyDpiperidines were also prepared through polyfluorination, and were used in the polyfluoroalkylation of aldehydes.

  DOI：

  10.3987/com-13-s(s)84

文献信息

• Pentafluoroethylation of Carbonyl Compounds Using HFC-125 in a Flow Microreactor System
  作者：Makoto Ono、Yuji Sumii、Yamato Fujihira、Takumi Kagawa、Hideyuki Mimura、Norio Shibata

  DOI：10.1021/acs.joc.1c00728

  日期：2021.10.15

  The protocol of micro-flow nucleophilic pentafluoroethylation using pentafluoroethane (HC2F5, HFC-125), a nontoxic, inexpensive, and commercially available greenhouse gas, is described. The micro-flow pentafluoroethylation by HFC-125 proceeded smoothly at room temperature or at −10 °C in DMF or toluene in the presence of a potassium base, namely, t-BuOK or KHMDS. A broad range of ketones, aldehydes

  描述了使用五氟乙烷 (HC 2 F 5 , HFC-125)的微流亲核五氟乙基化的协议，该协议是一种无毒、廉价且可商用的温室气体。HFC-125 的微流五氟乙基化在室温或-10°C 下在 DMF 或甲苯中在钾碱（即t- BuOK 或 KHMDS）存在下顺利进行。各种具有各种取代苯环的酮、醛和查耳酮立即成功地转化为相应的五氟乙基甲醇，产率很高。
• Nucleophilic Perfluoroalkylation of Aldehydes, Ketones, Imines, Disulfides, and Diselenides
  作者：Chaya Pooput、William R. Dolbier,、Maurice Médebielle

  DOI：10.1021/jo060250j

  日期：2006.4.1

  trifluoromethylation, the perfluoroalkyl anion reagents created by mixing C2F5I and n-C4F9I with tetrakis(dimethylamino)ethylene (TDAE) were effective in their nucleophilic reactions with aldehydes, ketones, imines, disulfides, and diselenides. Irradiation proved beneficial in the aldehyde and ketone reactions.

  使用类似于为亲核三氟甲基化开发的方法，通过将C 2 F 5 I和n -C 4 F 9 I与四（二甲基氨基）乙烯（TDAE）混合而产生的全氟烷基阴离子试剂在与醛，酮的亲核反应中有效，亚胺，二硫化物和二硒化物。辐射被证明对醛和酮反应有利。
• Polyfluoroalkylation of Carbonyl Compounds by Polyfluoroalkyl Anions Generated from Polyfluorcarboxamides
  作者：Shoji Hara、Natshumi Wakita

  DOI：10.3987/com-13-s(s)84

  日期：——

  Polyfluoroalkyl anions, generated by reduction of (polyfluoroalkanoyl)piperidines with Et3BHK, were used for the polyfluoroalkylation of carbonyl compounds. Trifluoromethylation of aromatic aldehydes proceeded in good yields, and that of aliphatic aldehydes afforded a moderate yield. In contrast, the yield was low when the reaction involved benzophenone. Pentafluoroethylation and octafluorobutylation of aldehydes were also carried out by using the corresponding (polyfluoroalkanoyl)piperidines, which were prepared from commercially available polyfluorocompounds. The (polyfluoroalkanoyDpiperidines were also prepared through polyfluorination, and were used in the polyfluoroalkylation of aldehydes.