1,1,2,2-tetrafluorononan-3-ol | 160016-74-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1,1,2,2-tetrafluorononan-3-ol
• CAS: 160016-74-0
• 化学式: C₉H₁₆F₄O
• 分子量: 216.219
• InChiKey: PIZASEYRHKCKAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,1,2,2-tetrafluoro-1-(phenylsulfonyl)nonan-3-ol 在 碘 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以74%的产率得到1,1,2,2-tetrafluorononan-3-ol
  参考文献：
  名称：

  Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

  摘要：

  Global interest in the "CF2CF2" building blocks (tetrafluoroethylene, tetrafluoroethyl) is still rather marginal. One of the main reasons is the lack of efficient and selective tetrafluoroethylation reagents. In this context, we present here three new reagents (PhSO2CF2CF2R, R = SiMe3, SiEt3 and H) capable of nucleophilic addition to carbonyl compounds, thus affording rare alcohols containing the CF2CF2 motif. The experimental observations are complemented with a brief computational study which confirmed that the reactivity of the nudeophilic reagents is strongly dependent on electronic properties of substituents on both ends of the CF2CF2 group. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.10.019

文献信息

• Development of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl-Substituted Alcohols and Tetrafluorotetrahydropyrans
  作者：Yana Chernykh、Katarina Hlat-Glembová、Blanka Klepetářová、Petr Beier

  DOI：10.1002/ejoc.201100667

  日期：2011.8

  PhSCF2CF2SiMe3 (1) was developed as a tandem anion and radical tetrafluoroethylene equivalent for the introduction of a CF2CF2 moiety. Fluoride-initiated nucleophilic additions of 1 to carbonyl compounds provide the corresponding alcohol adducts 2. Reduction of 2 gives tetafluoroethyl-containing alcohols 3, whereas 6-exo radical cyclizations of allyl ethers 4 yield tetrafluorotetrahydropyrans 5.

  PhSCF2CF2SiMe3 (1) 被开发为串联阴离子和自由基四氟乙烯等价物，用于引入 CF2CF2 部分。1 与羰基化合物的氟化物引发的亲核加成提供相应的醇加合物 2。 2 的还原产生含四氟乙基的醇 3，而烯丙基醚 4 的 6-外自由基环化产生四氟四氢吡喃 5。