4-fluoro-2,6-diphenyltetrahydro-2H-pyran | 131042-75-6

• 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: 4-fluoro-2,6-diphenyltetrahydro-2H-pyran
• CAS: 131042-75-6
• 化学式: C₁₇H₁₇FO
• 分子量: 256.32
• InChiKey: YPUFZNMLUGKUAQ-OSYLJGHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  苯甲醛 、 烯丙基三甲基硅烷 在 四氟硼酸-二乙醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以80%的产率得到4-fluoro-2,6-diphenyltetrahydro-2H-pyran
  参考文献：
  名称：

  HBF4·OEt2 as a versatile reagent for the Hosomi–Sakurai allylation and Prins cyclization: one-pot synthesis of symmetrical 4-fluorotetrahydropyrans

  摘要：

  The synthesis of symmetrical 2,6-disubstituted 4-fluorotetrahydropyran derivatives has been achieved using HBF4 center dot OEt2 via a tandem allylation and Prins cyclization. This is a highly efficient and diastereoselective approach for the preparation of 4-fluorotetrahydropyrans in a single step. The use of readily available and easy to handle reagent HBF4 center dot OEt2 makes this method simple, convenient and practical. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.082

文献信息

• Prins Cyclization in Ionic Liquid Hydrogen Fluoride Salts: Facile and Highly Efficient Synthesis of 4-Fluorinated Tetrahydropyrans, Thiacyclohexanes, and Piperidines
  作者：Yuichiro Kishi、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1002/ejoc.200800872

  日期：——

  Prins cyclization of homoallylic alcohols with various aldehydes was investigated in ionic liquid hydrogen fluoride (HF) salts, which played roles as a reaction medium, a catalyst, and a fluorine source. The reaction afforded the corresponding 4-fluorinated tetrahydropyrans in excellent yields with a high stereoselectivity (cis form exclusively). When benzaldehydes having a strongly electron-donating

  在离子液体氟化氢 (HF) 盐中研究了高烯丙醇与各种醛的 Prins 环化，该盐起到反应介质、催化剂和氟源的作用。该反应以优异的收率和高立体选择性（仅顺式形式）提供了相应的 4-氟化四氢吡喃。当使用在对位具有强给电子基团的苯甲醛时，该体系失去了立体选择性。为了将此方法应用于其他4-氟化杂环化合物的合成，我们还在HF盐中进行了thia-Prins和aza-Prins环化，分别成功地获得了4-氟化硫杂环己烷和哌啶。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Facile and highly efficient synthesis of fluorinated heterocycles via Prins cyclization in ionic liquid hydrogen fluoride salts
  作者：Yuichiro Kishi、Hirokatsu Nagura、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1039/b806389c

  日期：——

  Prins cyclization of homoallylic alcohols, thiols, and amines with various aldehydes in an ionic liquid HF salt (Et(4)NF.5HF) afforded the corresponding 4-fluorinated heterocycles in excellent yields.

  在离子液体HF盐（Et（4）NF.5HF）中，将均烯丙基醇，硫醇和胺与各种醛进行酯环化，从而以优异的收率得到相应的4-氟化杂环。