1-fluoro-2-methoxy-2-phenylpropane

• 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-fluoro-2-methoxy-2-phenylpropane
• 英文别名: (1-fluoro-2-methoxypropan-2-yl)benzene
• 化学式: C₁₀H₁₃FO
• 分子量: 168.211
• InChiKey: RJLOOPCIOZKZKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 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：
  2

反应信息

• 作为产物：
  描述：

  1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) 、 2-苯基-1-丙烯 以 甲醇 、 乙腈 为溶剂， 以85%的产率得到1-fluoro-2-methoxy-2-phenylpropane
  参考文献：
  名称：

  1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts and their

  摘要：

  本发明涉及1-取代-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐的制备和用途，特别是1-羟基-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐作为有机化合物中氟化试剂的引入剂。

  公开号：

  US05459267A1

文献信息

• 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate): An electrophilic fluorinating agent
  作者：Andrew J. Poss、George A. Shia

  DOI：10.1016/s0040-4039(99)00303-2

  日期：1999.4

  1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), NFTh, is a electrophilic fluorinating that can be used to fluorinate aromatic rings, olefins, dienol acetates and enol ethers. When NFTh is reacted with an active methylene compound in the presence of ZnCl2, the corresponding monoor di-fluoro derivative can be isolated.

  1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）NFTh是一种亲电子氟化剂，可用于氟化芳族环，烯烃，乙酸二烯醇酯和烯醇醚。当NFTh在ZnCl 2存在下与活性亚甲基化合物反应时，可以分离出相应的单或二氟衍生物。
• Process of fluorinating organic compounds with
  申请人：AlliedSignal Inc.

  公开号：US05606084A1

  公开（公告）日：1997-02-25

  The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.

  本发明涉及1-取代-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐的制备和用途，具体地说是1-羟基-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐作为有机化合物中氟原子引入的试剂。
• Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)
  作者：G. Sankar Lal

  DOI：10.1021/jo00062a023

  日期：1993.5

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.
• Stavber, Stojan; Pecan, Tjasa Sotler; Zupan, Marko, Journal of the Chemical Society. Perkin transactions II, 2000, # 6, p. 1141 - 1146
  作者：Stavber, Stojan、Pecan, Tjasa Sotler、Zupan, Marko

  DOI：——

  日期：——
• 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) as a new, effective reagent for selective fluorofunctionalisation of alkenes under mild reaction conditions
  作者：Stojan Stavber、Marko Zupan、Andrew J. Poss、George A. Shia

  DOI：10.1016/00404-0399(50)1337-h

  日期：1995.9

  1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor(TM) NFTh) is confirmed as a highly effective reagent for introducing a fluorine atom into organic molecules across a phenyl-substituted carbon-carbon double bond. Quantitative and Markovnikov-type regioselective formation of vicinal fluoro-hydroxy, fluoro-methoxy or fluoro-acetoxy adducts was achieved when phenyl-substituted alkenes were treated with a MeCN solution of NFTh in the presence of water, methanol or acetic acid. The stereochemical course of fluoro-methoxylation reactions in the case of cyclic phenyl-substituted alkenes depends strongly on the structure of the alkene.