benzyl 2-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 622853-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl 2-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: benzyl 2-fluoro-1-tetralone-2-carboxylate；benzyl 2-fluoro-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 622853-80-9；690267-68-6
• 化学式: C₁₈H₁₅FO₃
• 分子量: 298.314
• InChiKey: GYNYZNUKPYFQIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 palladium on activated charcoal 氢气 、 奎尼丁 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (R)-2-fluoro-3,4-dihydronaphthalen-1(2H)-one 、 (S)-2-fluoro-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Catalytic asymmetric protonation of fluoro-enolic species: access to optically active 2-fluoro-1-tetralone

  摘要：

  Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, (S)-(-)-2-fluoro-1-tetralone with up to 65% enantiomeric excess was obtained using quinine as the chiral base and Pd/C type 807104 from Merck as the heterogeneous catalyst. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00585-8
• 作为产物：
  描述：

  2-萘羧酸,1,2,3,4-四氢-1-羰基-,苯基甲基酯 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以69%的产率得到benzyl 2-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Catalytic asymmetric protonation of fluoro-enolic species: access to optically active 2-fluoro-1-tetralone

  摘要：

  Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, (S)-(-)-2-fluoro-1-tetralone with up to 65% enantiomeric excess was obtained using quinine as the chiral base and Pd/C type 807104 from Merck as the heterogeneous catalyst. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00585-8

文献信息

• 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
  作者：Aurélie Assalit、Thierry Billard、Stéphane Chambert、Bernard R. Langlois、Yves Queneau、Diane Coe

  DOI：10.1016/j.tetasy.2009.02.050

  日期：2009.3

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective fluorination of β-ketoesters catalysed by complexes of new mono-oxazoline ligands
  作者：Teng Niu、Xiping Han、Danfeng Huang、Ke-Hu Wang、Yingpeng Su、Yulai Hu、Ying Fu

  DOI：10.1016/j.jfluchem.2015.02.017

  日期：2015.7

  A new kind of mono-oxazoline ligands which combined diaryl methyl units and chiral oxazoline units together using pyridine as linker was prepared. Their applications in enantioselective electrophilic fluorination of beta-ketoesters by NFSI were investigated, and the corresponding products were obtained in excellent yield (up to 90%) and good enantioselectivity (78%) in CH2Cl2 at -60 degrees C. (C) 2015 Elsevier B.V. All rights reserved.
• Catalytic asymmetric protonation of fluoro-enolic species: access to optically active 2-fluoro-1-tetralone
  作者：Markus A. Baur、Abdelkhalek Riahi、Françoise Hénin、Jacques Muzart

  DOI：10.1016/s0957-4166(03)00585-8

  日期：2003.9

  Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, (S)-(-)-2-fluoro-1-tetralone with up to 65% enantiomeric excess was obtained using quinine as the chiral base and Pd/C type 807104 from Merck as the heterogeneous catalyst. (C) 2003 Elsevier Ltd. All rights reserved.