2-fluoro-1-methoxy-1-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: 2-fluoro-1-methoxy-1-phenylpropane
• 英文别名: (2-Fluoro-1-methoxypropyl)benzene
• 化学式: C₁₀H₁₃FO
• 分子量: 168.211
• InChiKey: UYHJEZIBLDYCKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 作为反应物：
  描述：

  2-fluoro-1-methoxy-1-phenylpropane 、 triethylboronlithium hydride 、 四氢呋喃 生成 (1-methoxypropyl)benzene
  参考文献：
  名称：

  BRANDAENGE, S.;DAHLMAN, O.;OELUND, J., ACTA CHEM. SCAND., 1983, 37, N 2, 141-145

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-氟苯基)-1-丙酮 在 sodium tetrahydroborate 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-fluoro-1-methoxy-1-phenylpropane
  参考文献：
  名称：

  Brandaenge, Svante; Dahlman, Olof; Oelund, Jonas, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 2, p. 141 - 146

  摘要：

  DOI：

文献信息

• Stereochemistry and Some Kinetic Aspects of Fluorination of Phenyl-Substituted Alkenes with Selectfluor^TMReagent F-TEDA-BF₄
  作者：Stojan Stavber、Tjaša Sotler-Pecan、Marko Zupan

  DOI：10.1246/bcsj.69.169

  日期：1996.1

  while equal amounts of both diastereoisomers were formed in the case of (E)-1-phenyl-1-propene and acenaphthylene. In the phenyl-substituted benzocyclene series the stereochemistry of fluoro-alkoxylation was found to be dependent on ring size and on the structure of the alcohol. The resulting vicinal fluoroalkoxy adducts were transformed by heating in aqueous HBr to 2-fluoro-1-phenylbenzocyclenes. Correlation

  在各种醇存在下，苯基取代的烯烃与 SelectfluorTM 氟化试剂 F-TEDA-BF4 的反应导致形成具有 Markovnikov 类型区域选择性的邻位氟烷氧基加合物。发现氟甲氧基加成反应的立体化学在 (Z)-茋、茚和二苯并丁二烯酮的情况下略占优势，而在 (E)-1-苯基的情况下形成等量的两种非对映异构体-1-丙烯和苊。在苯基取代的苯并环烯系列中，发现氟烷氧基化的立体化学取决于环的大小和醇的结构。所得的邻位氟烷氧基加合物通过在 HBr 水溶液中加热转化为 2-氟-1-苯基苯并环烯。
• <i>N</i>,<i>N</i>′-Difluoro-1,4-diazoniabicyclo[2.2.2]octane Salts, Highly Reactive and Easy-to-Handle Electrophilic Fluorinating Agents
  作者：Teruo Umemoto、Masayuki Nagayoshi

  DOI：10.1246/bcsj.69.2287

  日期：1996.8

  A series of N,N′-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts were synthesized in a pure form by the fluorination of 1,4-diazabicyclo[2.2.2]octane with F2 diluted with N2 in the presence of a Brønsted acid in fluoro alcohol or acetonitrile or by fluorination followed by a treatment with a different Brønsted or Lewis acid. Their complete structural assignment was made based on spectral and elemental analyses of the isolated crystals. A great through-bond interaction between the two N–F’s of the salt was observed on 19F NMR. An assessment was made of the usefulness of N,N′-difluoro-1,4-diazoniabicyclo[2.2.2]octane bis(triflate), bis(HSO4), bis(BF4), and bis(SbF6) salts for electrophilic fluorination; the bis(BF4) salt was demonstrated to be widely applicable as a highly reactive and easy-to-handle fluorinating agent. Thus, the bis(BF4) salt readily fluorinated activated aromatics, active methylene compounds or their salts, substituted styrenes, and vinyl acetates under mild conditions. It was shown that one N–F of the salt was effective for fluorination and that the other N–F played a role to activate fluorination through the bonds. Thus, the reaction mechanism was discussed, and fluorination followed by an immediate intramolecular one-electron transfer was suggested.

  在氟化醇或乙腈中，在一种布氏酸的存在下，用用 N2 稀释的 F2 对 1,4-二氮杂双环[2.2.2]辛烷进行氟化处理，或在氟化后再用不同的布氏酸或路易斯酸进行处理，从而合成了一系列 N,N′-二氟-1,4-二氮杂双环[2.2.2]辛烷纯盐。根据对分离晶体的光谱和元素分析，对它们进行了完整的结构鉴定。19F NMR 观察到盐的两个 N-F之间存在巨大的直通键相互作用。对 N,N′-二氟-1,4-二氮杂双环[2.2.2]辛烷双(三氯酸盐)、双(HSO4)、双(BF4)和双(SbF6)盐的亲电氟化作用进行了评估。因此，在温和的条件下，双（ ）盐很容易氟化活化芳烃、活性亚甲基化合物或其盐、取代苯乙烯和乙酸乙烯酯。研究表明，该盐中的一个 N-F 对氟化有效，而另一个 N-F 则通过键来激活氟化。因此，对反应机理进行了讨论，并提出了氟化之后立即发生分子内单电子转移的观点。
• Evidence for the existence of methyl hypofluorite: methanolysis of xenon difluoride
  作者：Dale F. Shellhamer、Carol M. Curtis、Don R. Hollingsworth、Mark L. Ragains、Ruthann E. Richardson、Victor L. Heasley、Gene E. Heasley

  DOI：10.1016/s0040-4039(00)87287-1

  日期：——

  Methyl hypofluorite is indicated as an intermediate in the reaction of xenon difluoride with alkenes in methanol as solvent.

  次氟甲烷指示为在甲醇作为溶剂的二氟化氙与烯烃反应中的中间体。
• SHELLHAMER, D. F.;CURTIS, C. M.;HOLLINGSWORTH, D. R.;RAGAINS, M. L.;RICHA+, TETRAHEDRON LETT., 1982, 23, N 21, 2157-2160
  作者：SHELLHAMER, D. F.、CURTIS, C. M.、HOLLINGSWORTH, D. R.、RAGAINS, M. L.、RICHA+

  DOI：——

  日期：——