2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester | 637041-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester
• 英文别名: ethyl 2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylate；Ethyl 2-fluoro-2-(4-methoxyphenyl)cyclopropane-1-carboxylate；ethyl 2-fluoro-2-(4-methoxyphenyl)cyclopropane-1-carboxylate
• CAS: 637041-14-6
• 化学式: C₁₃H₁₅FO₃
• 分子量: 238.259
• InChiKey: YUNNXIODRLJOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester 以24%的产率得到2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.06.048
• 作为产物：
  描述：

  2-(4-Methoxy-phenyl)-2-trimethylsilanyloxy-cyclopropanecarboxylic acid ethyl ester 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到2-fluoro-2-(4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  叔环丙基甲硅烷基醚与二乙基氨基三氟化硫的反应：取代基对环丙烷环裂解的影响

  摘要：

  叔环丙醇甲硅烷基醚与二乙基氨基三氟化硫的反应通常引起开环以产生烯丙基氟化物。然而，在C 1处带有强供电子取代基或在C 2上具有吸电子取代基的环丙基甲硅烷基醚不能提供烯丙基氟化物，而是氟代环丙烷。还已经证明，叔环丙醇甲硅烷基醚的C 2上的供电子取代基在与二乙氨基硫三氟化物的反应中促进开环。

  DOI：

  10.1016/j.tetlet.2003.09.089

文献信息

• Diastereoselectivity of cyclopropanation of substituted α-fluorostyrenes versus styrenes by different methods
  作者：Katharina Bartels、Benjamin Schinor、Günter Haufe

  DOI：10.1016/j.jfluchem.2017.09.008

  日期：2017.11

  respectively, were obtained. An advantage of the latter protocol is the in situ formation of ethyl diazoacetate from ethyl glycinate hydrochloride in aqueous solution by diazotation avoiding the in-substance application of the potentially explosive ethyl diazoacetate. Accordingly, a series of diastereoisomeric ethyl 2-aryl-2-fluoro-cyclopropane carboxylates was synthesized from p- or m-substituted α-fluorostyrenes

  苯乙烯和α-氟苯乙烯与重氮乙酸酯的环丙烷化的非对映选择性取决于所用催化剂以及氟取代基的存在与否。苯乙烯与重氮乙酸酯的Cu（acac）2催化反应产生3：1的选择性，有利于反式-2-苯基环丙烷羧酸酯，而α-氟苯乙烯则提供了1：1的顺式/反式异构体混合物。竞争实验证明，与苯乙烯本身相比，α-氟苯乙烯的反应更慢。用较大的四苯基铁（III）-卟啉氯化物作为催化剂，分别得到10∶1或3∶1的混合物。后一种协议的优点是原位通过重氮化从水溶液中的甘氨酸乙酯盐酸盐中生成重氮乙酸乙酯，从而避免了潜在爆炸性的重氮乙酸乙酯的实质性应用。因此，非对映异构系列2-芳基-2-氟-环丙烷羧酸的合成自p -或米取代α-氟苯乙烯。
• 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.
• Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride: the effects of substituents on the cleavage of the cyclopropane ring
  作者：Masayuki Kirihara、Hiroko Kakuda、Makoto Tsunooka、Akihiro Shimajiri、Tomofumi Takuwa、Akihiko Hatano

  DOI：10.1016/j.tetlet.2003.09.089

  日期：2003.11

  The reaction of tertiary cyclopropanol silyl ethers with diethylaminosulfur trifluoride usually causes ring opening to produce allylic fluorides. However, cyclopropyl silyl ethers bearing a strong electron-donating substituent at C1 or an electron-withdrawing substituent at C2 do not afford allylic fluorides but fluorocyclopropanes. It has also been proved that an electron-donating substituent at C2

  叔环丙醇甲硅烷基醚与二乙基氨基三氟化硫的反应通常引起开环以产生烯丙基氟化物。然而，在C 1处带有强供电子取代基或在C 2上具有吸电子取代基的环丙基甲硅烷基醚不能提供烯丙基氟化物，而是氟代环丙烷。还已经证明，叔环丙醇甲硅烷基醚的C 2上的供电子取代基在与二乙氨基硫三氟化物的反应中促进开环。