N-methyl-1-(naphthalen-1-yl)ethan-1-imine | 194040-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-1-(naphthalen-1-yl)ethan-1-imine
• 英文别名: N-(1-(naphthalen-1-yl)ethylidene)methanamine；N-methyl-1-naphthalen-1-ylethanimine
• CAS: 194040-82-9
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: QUTMGIYLBMOXHD-UHFFFAOYSA-N

物化性质

• 沸点：
  293.5±13.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-1-(naphthalen-1-yl)ethan-1-imine 在 potassium carbonate 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成
  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：

  1-萘乙酮 、 甲胺 以 甲醇 为溶剂， 反应 8.0h， 以91%的产率得到N-methyl-1-(naphthalen-1-yl)ethan-1-imine
  参考文献：
  名称：

  [EN] A PROCESS FOR THE PREPARATION OF CINACALCET AND ITS SALTS
  [FR] PROCÉDÉ DE PRÉPARATION DE CINACALCET ET SES SELS

  摘要：

  公开号：

  WO2010010359A3

文献信息

• Microwave assisted fluorination: an improved method for side chain fluorination of substituted 1-arylethanones
  作者：Thor Håkon Krane Thvedt、Erik Fuglseth、Eirik Sundby、Bård Helge Hoff

  DOI：10.1016/j.tet.2009.09.070

  日期：2009.11

  microwave (MW) assisted fluorination of 1-arylethanones to their corresponding 1-aryl-2-fluoroethanones has been developed. The first step utilises Selectfluor™ as a fluorinating agent in methanol forming 1-aryl-2-fluoroethanones and their corresponding dimethyl acetals. In the second step, water is added and Selectfluor™ acts as a Lewis acid in the hydrolytic cleavage of the dimethyl acetals. Compared to

  已经开发了一种两步一锅微波（MW）辅助将1-蒽酮氟化为相应的1-芳基-2-氟乙酮的方法。第一步利用Selectfluor™作为甲醇中的氟化剂，形成1-芳基-2-氟乙酮及其相应的二甲基乙缩醛。在第二步中，添加水，并且Selectfluor™在二甲基乙缩醛的水解裂解中充当路易斯酸。与热合成相比，MW辅助方法可减少氟化反应和二甲基乙缩醛反应的反应时间。而且，一锅法减少了试剂和溶剂的消耗。该方法最适合于制备含有可钝化亲电芳族取代基的取代基的1-芳基-2-氟乙酮，但高度缺电子的酮如1-（3，5-二硝基苯基）乙酮反应更慢。使用富含电子的芳族酮进行的反应具有较低的区域选择性，并且还产生了氟代芳族产物。
• Stereogenic Lock in 1-Naphthylethanamine Complexes for Catalyst and Auxiliary Design: Structural and Reactivity Analysis for Cycloiridated Pseudotetrahedral Complexes
  作者：Houguang Jeremy Chen、Ronald Hong Xiang Teo、Yongxin Li、Sumod A. Pullarkat、Pak-Hing Leung

  DOI：10.1021/acs.organomet.7b00760

  日期：2018.1.8

  derivative, the structural lock prevented oxidation of the amine moiety within the five-membered organometallic ring during its synthesis. With up to three stereogenic centers in one of the naphthalene complexes, the stereochemistry of the metallacycle remained stable to both thermal and chemical changes. In terms of catalytic performance, the complexes displayed excellent activity for the asymmetric hydrogen

  制备了一系列光学活性的拟四面体五元环金属化的1-萘基胺铱（III）配合物，并对其进行了表征，以分析固相和溶液相中立体构象锁的功效。iridacycles的合成是非对映选择性的，并且发现这些化合物在构象上是刚性的。与它的苯基衍生物相比，结构锁防止了五元有机金属环中胺部分在合成过程中的氧化。在一种萘配合物中最多有三个立体异构中心，金属环的立体化学对热和化学变化均保持稳定。在催化性能方面，络合物对不对称氢转移反应显示出优异的活性，
• [EN] A PROCESS FOR THE PREPARATION OF CINACALCET AND ITS SALTS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CINACALCET ET SES SELS
  申请人：CILPA LTD

  公开号：WO2010010359A3

  公开（公告）日：2010-03-18
• 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.