N-[2,2-difluoro-1-(1-naphthyl)ethyl]-N-methylamine | 1200401-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2,2-difluoro-1-(1-naphthyl)ethyl]-N-methylamine
• 英文别名: 2,2-difluoro-N-methyl-1-naphthalen-1-ylethanamine
• CAS: 1200401-11-1
• 化学式: C₁₃H₁₃F₂N
• 分子量: 221.25
• InChiKey: OJEHEBBXLSIBFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2,2-difluoro-1-(1-naphthyl)ethyl]-N-methylamine 、 4-叔丁基苄溴 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以90%的产率得到N-(4-tert-butylbenzyl)-2,2-difluoro-N-methyl-1-(naphthalen-1-yl)ethanamine
  参考文献：
  名称：

  Chiral derivatives of Butenafine and Terbinafine: synthesis and antifungal activity

  摘要：

  Two series of allylamines/benzylamines have been synthesised and evaluated for their antifungal activity towards Cryptococcus neoformans. All compounds are chiral derivatives of Butenafine and Terbinafine, having additional substituents at the carbon connected to the central nitrogen atom. In both series. the antifungal activity was strongly dependent on both the steric bulk and the electronic nature of the substituents. Compared to the parent compounds (Butenafine and Terbinafine), the activity was maintained when the hydrogen was replaced with a methyl group. Lower activity was observed for ethyl, whereas introduction of -CH2F, -CHF2, -CF3 or -CN substituents removed all antifungal activity. Testing of (R)- and (S)-N-(4-tert-butylbenzyl)-N-methyl-1-(naphthalen-1-yl)ethanamine against C. neoformans. Cryptococcus diffluens and Trichosporon cutaneum revealed that most of the activity resides in the (R)-enantiomer. The (R)-enantiomer performed as well as, or better (lower MIC values) than Butenafine against each test strain, suggesting that antimycotics based on this compound might be an improvement of existing Butenafine-based formulations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.067
• 作为产物：
  描述：

  在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以0.56 g的产率得到N-[2,2-difluoro-1-(1-naphthyl)ethyl]-N-methylamine
  参考文献：
  名称：

  Chiral derivatives of Butenafine and Terbinafine: synthesis and antifungal activity

  摘要：

  Two series of allylamines/benzylamines have been synthesised and evaluated for their antifungal activity towards Cryptococcus neoformans. All compounds are chiral derivatives of Butenafine and Terbinafine, having additional substituents at the carbon connected to the central nitrogen atom. In both series. the antifungal activity was strongly dependent on both the steric bulk and the electronic nature of the substituents. Compared to the parent compounds (Butenafine and Terbinafine), the activity was maintained when the hydrogen was replaced with a methyl group. Lower activity was observed for ethyl, whereas introduction of -CH2F, -CHF2, -CF3 or -CN substituents removed all antifungal activity. Testing of (R)- and (S)-N-(4-tert-butylbenzyl)-N-methyl-1-(naphthalen-1-yl)ethanamine against C. neoformans. Cryptococcus diffluens and Trichosporon cutaneum revealed that most of the activity resides in the (R)-enantiomer. The (R)-enantiomer performed as well as, or better (lower MIC values) than Butenafine against each test strain, suggesting that antimycotics based on this compound might be an improvement of existing Butenafine-based formulations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.067

文献信息

• Reactions of Sulfur- and Phosphorus-Substituted Fluoroalkylating Silicon Reagents with Imines and Enamines under Acidic Conditions
  作者：Mikhail D. Kosobokov、Alexander D. Dilman、Marina I. Struchkova、Pavel A. Belyakov、Jinbo Hu

  DOI：10.1021/jo202669w

  日期：2012.2.17

  Nucleophilic fluoroalkylation reactions of imines and enamines with alpha-phenylthio, alpha-phenylsulfonyl, and alpha-diethylphosphoryl substituted fluorinated silanes have been investigated. The reactions are promoted by hydrofluoric acid generated in situ from potassium hydrodifluoride and trifluoroacetic acid. Sulfur reagents worked well with both imines and enamines, whereas phosphorus reagent efficiently coupled only with enamines.
• Chiral derivatives of Butenafine and Terbinafine: synthesis and antifungal activity
  作者：Erik Fuglseth、Eli Otterholt、Hanne Høgmoen、Eirik Sundby、Colin Charnock、Bård Helge Hoff

  DOI：10.1016/j.tet.2009.09.067

  日期：2009.11

  Two series of allylamines/benzylamines have been synthesised and evaluated for their antifungal activity towards Cryptococcus neoformans. All compounds are chiral derivatives of Butenafine and Terbinafine, having additional substituents at the carbon connected to the central nitrogen atom. In both series. the antifungal activity was strongly dependent on both the steric bulk and the electronic nature of the substituents. Compared to the parent compounds (Butenafine and Terbinafine), the activity was maintained when the hydrogen was replaced with a methyl group. Lower activity was observed for ethyl, whereas introduction of -CH2F, -CHF2, -CF3 or -CN substituents removed all antifungal activity. Testing of (R)- and (S)-N-(4-tert-butylbenzyl)-N-methyl-1-(naphthalen-1-yl)ethanamine against C. neoformans. Cryptococcus diffluens and Trichosporon cutaneum revealed that most of the activity resides in the (R)-enantiomer. The (R)-enantiomer performed as well as, or better (lower MIC values) than Butenafine against each test strain, suggesting that antimycotics based on this compound might be an improvement of existing Butenafine-based formulations. (C) 2009 Elsevier Ltd. All rights reserved.