1-fluoro-2-methoxy-1,1,2,2-tetraphenylethane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-fluoro-2-methoxy-1,1,2,2-tetraphenylethane
• 英文别名: 2-fluoro-1-methoxy-1,1,2,2-tetraphenylethane；(1-Fluoro-2-methoxy-1,2,2-triphenylethyl)benzene
• 化学式: C₂₇H₂₃FO
• 分子量: 382.477
• InChiKey: GBMXGWLOWHBRNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  甲醇 、 1,1,2,2-四苯乙烯 在 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) 作用下， 以 乙腈 为溶剂， 生成 1-fluoro-2-methoxy-1,1,2,2-tetraphenylethane
  参考文献：
  名称：

  反应条件对使用Accufluor™NFTh将氟轻度引入苯基取代的烯烃中的动力学和活化参数的影响

  摘要：

  提出了从F–L型试剂（亲电氟化试剂）进行轻度氟转移的双分子过程的证据。在24°C于甲醇中的1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）（NFTh）中氟化苯基取代的烯烃的相应二级速率常数作为亲核试剂，得到邻位氟甲氧基加成物用马氏型区域选择性的，有：ķ 2 = 9.1×10 -3 中号-1 小号-1为1,1-二苯基乙烯（1），2.7×10 -2 中号-1  š -1为triphenylethene（2），2.0×10 -2 中号-1  š -1为四苯乙烯（3），5.5×10 -3 中号-1 小号-1为苊烯（7）和4.7×10 -3 中号-1 小号- 1 9 - benzylidenefluorene（10A）。用甲醇代替亲核试剂代替水对过程速率以及溶剂极性的变化影响可忽略不计，表明与反应物相比，决定速率的过渡态的极性变化很小。活化焓（介于62和74 kJ mol -1之间）和活化能（介于-75和-37

  DOI：

  10.1016/s0040-4020(00)00109-5

文献信息

• Effect of Reaction Conditions on the Kinetic and Activation Parameters for the Mild Introduction of Fluorine into Phenyl-Substituted Alkenes with Accufluor™ NFTh
  作者：Stojan Stavber、Tjaša Sotler Pečan、Marko Zupan

  DOI：10.1016/s0040-4020(00)00109-5

  日期：2000.3

  water had a negligible effect on the rate of the process, as well as the change of solvent polarity, indicating little change in the polarity of the rate-determining transition state in comparison with the reactants. Activation enthalpies (between 62 and 74 kJ mol−1) and activation enthropies (between −75 and −37 J mol−1 K−1) were determined for fluorination of 1 and 7 with NFTh in acetonitrile in the

  提出了从F–L型试剂（亲电氟化试剂）进行轻度氟转移的双分子过程的证据。在24°C于甲醇中的1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）（NFTh）中氟化苯基取代的烯烃的相应二级速率常数作为亲核试剂，得到邻位氟甲氧基加成物用马氏型区域选择性的，有：ķ 2 = 9.1×10 -3 中号-1 小号-1为1,1-二苯基乙烯（1），2.7×10 -2 中号-1  š -1为triphenylethene（2），2.0×10 -2 中号-1  š -1为四苯乙烯（3），5.5×10 -3 中号-1 小号-1为苊烯（7）和4.7×10 -3 中号-1 小号- 1 9 - benzylidenefluorene（10A）。用甲醇代替亲核试剂代替水对过程速率以及溶剂极性的变化影响可忽略不计，表明与反应物相比，决定速率的过渡态的极性变化很小。活化焓（介于62和74 kJ mol -1之间）和活化能（介于-75和-37
• A mild, selective method for preparation of vicinal fluoro ethers using “F-Teda-BF4”
  作者：Stojan Stavber、Tjasa Sotler、Marko Zupan

  DOI：10.1016/s0040-4039(00)79977-1

  日期：1994.2

  Vicinal alkoxy fluorides are efficiently formed by room temperature reaction of phenyl substituted alkenes with commercially available 1-chloromethyl-4-fluoro-1,4-diazobicyclo[2.2.2]octane bis tetrafluoroborate (Selectfluor(TM) F-Teda BF4) in CH3CN in the presence of various alcohols. The reaction follows Markovnikov-type regioselectivity, while stereoselectivity in the case of phenyl substituted benzocyclenes strongly depends on the ring size and the structure of the alcohol.
• 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.
• Zupan, Marko; Metelko, Maja; Stavber, Stojan, Journal of the Chemical Society. Perkin transactions I, 1993, # 22, p. 2851 - 2856
  作者：Zupan, Marko、Metelko, Maja、Stavber, Stojan

  DOI：——

  日期：——
• Investigation of Radical Cation in Electrophilic Fluorination by ESI-MS
  作者：Xiang Zhang、Yuanxi Liao、Rong Qian、Haoyang Wang、Yinlong Guo

  DOI：10.1021/ol051281o

  日期：2005.9.1

  Reaction solutions of selectfluor (1) with triphenylethylene (4a) and tetraphenylethylene (4b) were monitored by ESI-MS and ESI-MS/MS. Detection and characterization of the key radical cationic intermediates 5a(center dot+) and 5b(center dot+) fully supports the SET mechanism in electrophilic fluorination as depicted above.