2-bromo-1-fluoro-1-(4-methoxyphenyl)ethane | 66472-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-1-fluoro-1-(4-methoxyphenyl)ethane
• 英文别名: 1-(2-bromo-1-fluoroethyl)-4-methoxybenzene
• CAS: 66472-42-2
• 化学式: C₉H₁₀BrFO
• 分子量: 233.08
• InChiKey: DNNGYSNGPXZWLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-bromo-1-fluoro-1-(4-methoxyphenyl)ethane 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以2.32 g的产率得到1-(1-氟乙烯基)-4-甲氧基苯
  参考文献：
  名称：

  氟化环丙烷：芳基α，β，β-三氟环丙烷基序的合成与化学†

  摘要：

  报道了制备芳基α，β，β-三氟环丙烷的一般路线，芳基氧化得到相应的α，β，β-三氟环丙烷羧酸。相应的酰胺与苯酚/硫代苯酚的反应导致HF的消除，然后共轭物的添加。尽管有三个碳原子，部分氟化的环丙烷具有与–CF 3相似的亲脂性，并且它作为药物发现的新主题而出现。

  DOI：

  10.1039/c8cc04964e
• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 N,N-二甲基丙烯基脲 、 N-溴代丁二酰亚胺(NBS) 、 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到2-bromo-1-fluoro-1-(4-methoxyphenyl)ethane
  参考文献：
  名称：

  使用DMPU / HF作为氟化试剂对不饱和化合物进行溴氟化

  摘要：

  溴氟化反应是通过用N-溴琥珀酰亚胺（NBS）和DMPU / HF作为氟化试剂处理各种不饱和化合物来进行的。DMPU / HF络合物显示出是一种有效的氟化试剂，可将烯烃转化为其相应的溴氟化合物。它显示出高反应性，并且该方法提供了具有良好马尔科夫尼科夫区域选择性的溴氟化产物。这些氟化化合物是有用的起始原料，并充当许多氟化生物活性分子的基础。

  DOI：

  10.1016/j.jfluchem.2017.07.016

文献信息

• Fluorinated phenylcyclopropylamines. Part 5: Effects of electron-withdrawing or -donating aryl substituents on the inhibition of monoamine oxidases A and B by 2-aryl-2-fluoro-cyclopropylamines
  作者：Svenja Hruschka、Thomas C. Rosen、Shinichi Yoshida、Kenneth L. Kirk、Roland Fröhlich、Birgit Wibbeling、Günter Haufe

  DOI：10.1016/j.bmc.2008.06.048

  日期：2008.8

  A series of racemic, diastereoisomeric aryl cyclopropylamines substituted with fluorine in the 2-position and electron-donating and electron-withdrawing groups on the aromatic ring have been prepared. These represent analogues of the classic MAO inhibitor tranylcypromine (trans-2-phenylcyclopropylamine, 1). Their activities as inhibitors of recombinant human liver monoamine oxidases A (MAO A) and B (MAO B) were determined. The trans-compounds were low micromolar inhibitors of both MAO A and MAO B with moderate MAO A selectivity while the less active cis-analogues were MAO B selective. In the trans-series, electron-withdrawing para-substituents increased the potency of MAO A inhibition while electron-donating groups such as methyl or methoxy had no influence on this activity. In contrast, aromatic ring substitution in the trans-series had essentially no effect on the inhibition of MAO B. The corresponding cis-compounds were shown to be 10-100 times less active against MAO A, while trans-and cis-compounds were quite similar in terms of inhibition of MAO B. The best MAO A/ MAO B selectivity (7: 1) in the trans-series was found for trans-2-fluoro-2-(para-trifluoromethylphenyl) cyclopropylamine (7d), while a 1: 27 selectivity was found for cis-2-fluoro-2-(para-fluorophenyl) cyclopropylamine (10c). These results are discussed in connection with the pK(a) and logD values, the mechanism of action of tranylcypromines, and the geometry of the active site of the enzymes. (C) 2008 Elsevier Ltd. All rights reserved.
• Herstellung von Vinylfluoriden
  作者：Lothar ECKES、Michael HANACK

  DOI：10.1055/s-1978-24713

  日期：——