2-(methoxymethyl)-amino-1,4-naphthoquinone | 1443104-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(methoxymethyl)-amino-1,4-naphthoquinone
• 英文别名: 2-(methoxymethylamino)-1,4-naphthoquinone；2-(Methoxymethylamino)naphthalene-1,4-dione；2-(methoxymethylamino)naphthalene-1,4-dione
• CAS: 1443104-06-0
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: HNJOHOPXFFCSOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-萘醌 在 sodium azide 、 水 、 lithium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 2-(methoxymethyl)-amino-1,4-naphthoquinone
  参考文献：
  名称：

  利用烷氧基甲基氯对2-羟基-1,4-萘醌衍生物进行非常规的化学选择性醚化：范围，机理和在合成具有生物活性的天然产物（±）-lantalucratin C中的应用

  摘要：

  描述了2-羟基-1，4-萘醌衍生物与烷氧基烷基氯化物和氢化物碱的新型醚化。对条件和底物范围的精确研究表明，该反应特别发生在具有2-羟基-1,4-苯醌骨架的分子中。实现了化学选择性的O-甲基化反应，以提供合成上重要的中间体，该中间体可轻松获得具有抗肿瘤活性的天然产物。

  DOI：

  10.1016/j.tet.2016.01.040

文献信息

• Synthesis using microwave irradiation and antibacterial evaluation of new N,O-acetals and N,S-acetals derived from 2-amino-1,4-naphthoquinones
  作者：Alessandro K. Jordão、Juliana Novais、Bruno Leal、Ana C. Escobar、Helvécio M. dos Santos Júnior、Helena C. Castro、Vitor F. Ferreira

  DOI：10.1016/j.ejmech.2013.01.010

  日期：2013.5

  This paper describes a novel series of N,O-acetals and N,S-acetals (7a-o) derived from 2-amino-1,4-naphthoquinones that were synthesized and evaluated as potential antimicrobial agents. These compounds were obtained in good yields using microwave irradiation, and several of them showed promising antibacterial profiles. Three of our biologically active 2-amino-1,4-naphthoquinone N,O-acetals and N,S-acetals tested against hospital bacterial strains were identified as potential lead compounds. Characterization of all compounds was performed using one-dimensional NMR techniques (H-1, C-13-APT), IR spectra, elemental analyses and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). (C) 2013 Published by Elsevier Masson SAS.
• Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C
  作者：Tokutaro Ogata、Tomoyo Yoshida、Maki Shimizu、Manami Tanaka、Chie Fukuhara、Junko Ishii、Arisa Nishiuchi、Kiyofumi Inamoto、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2016.01.040

  日期：2016.3

  A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered

  描述了2-羟基-1，4-萘醌衍生物与烷氧基烷基氯化物和氢化物碱的新型醚化。对条件和底物范围的精确研究表明，该反应特别发生在具有2-羟基-1,4-苯醌骨架的分子中。实现了化学选择性的O-甲基化反应，以提供合成上重要的中间体，该中间体可轻松获得具有抗肿瘤活性的天然产物。