1-甲基-2-[(4-硝基苯氧基)甲基]苯 | 92199-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲基-2-[(4-硝基苯氧基)甲基]苯
• 英文名称: 2-methylbenzyl-4-nitrophenyl ether
• 英文别名: (4-Nitro-phenyl)-(2-methyl-benzyl)-ether；1-Methyl-2-[(4-nitrophenoxy)methyl]benzene
• CAS: 92199-99-0
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: UVZXKWFFFXEFCB-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  401.9±25.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-2-[(4-硝基苯氧基)甲基]苯 在 甲酸 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， -3.0~20.0 ℃ 、500.01 kPa 条件下， 反应 0.5h， 生成 6-[(2-methylbenzyl)oxy]-1,3-benzothiazol-2-amine
  参考文献：
  名称：

  1,3-Benzothiazoles as Antimicrobial Agents

  摘要：

  Starting from 2-amino-1,3-mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2-mercapto-1,3-benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2-position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure-activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6-position of the aryl moiety showed high antifungal activity.

  DOI：

  10.1002/jhet.2222
• 作为产物：
  描述：

  邻甲基氯化苄 、 4-nitrophenol sodium salt 生成 1-甲基-2-[(4-硝基苯氧基)甲基]苯
  参考文献：
  名称：

  脱甲基研究。IV。烷基-和芳基-对-硝基苯醚的体外和体内裂解。

  摘要：

  DOI：

  10.1021/jm00340a001

文献信息

• Iron-catalyzed oxidative etherification of benzylic C(sp3)–H bonds with phenols
  作者：Bei Li、Yang Liu、Yan-Ling Song、Hong-Mei Sun

  DOI：10.1016/j.tetlet.2023.154690

  日期：2023.9

  present work provides a general protocol with high levels of step- and atom-economy for the synthesis of aryl ethers, particularly for aryl benzyl ethers. The direct use of toluene and phenols as starting materials also renders this protocol as a novel strategy for the protection of hydroxyl groups presented in various phenols.

  通过使用容易获得的离子 Fe(III) 配合物 [HIPym][FeBr 4 ] 作为催化剂和 DTBP 作为氧化剂，实现了苯甲基 C(sp 3 )–H 键与酚的首次氧化醚化。目前的工作为芳基醚，特别是芳基苄基醚的合成提供了一种具有高水平步骤经济性和原子经济性的通用方案。直接使用甲苯和苯酚作为起始原料也使该方案成为保护各种苯酚中存在的羟基的新策略。
• Demethylation Studies. IV. The in vitro and in vivo Cleavage of Alkyl- and Arylalkyl-p-nitrophenyl Ethers
  作者：Robert E. McMahon、Hilman W. Culp、Jack Mills、Frederick J. Marshall

  DOI：10.1021/jm00340a001

  日期：1963.7
• 1,3-Benzothiazoles as Antimicrobial Agents
  作者：Ivana Defrenza、Alessia Catalano、Alessia Carocci、Antonio Carrieri、Marilena Muraglia、Antonio Rosato、Filomena Corbo、Carlo Franchini

  DOI：10.1002/jhet.2222

  日期：2015.11

  Starting from 2-amino-1,3-mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2-mercapto-1,3-benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2-position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure-activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6-position of the aryl moiety showed high antifungal activity.