2,6-dimethoxybenzohydroxamic acid | 51410-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethoxybenzohydroxamic acid
• 英文别名: N-hydroxy-2,6-dimethoxybenzamide；2.6-Dimethoxybenzohydroxamsaeure；2,6-Dimethoxybenzenecarbohydroxamic acid
• CAS: 51410-99-2
• 化学式: C₉H₁₁NO₄
• mdl: MFCD09928732
• 分子量: 197.191
• InChiKey: UCSCCSDEGMOIQL-UHFFFAOYSA-N

物化性质

• 熔点：
  201.2-201.5 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxybenzohydroxamic acid 在 乙酸酐 、 potassium carbonate 、 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 0.17h， 以93%的产率得到2,6-二甲氧基苯胺
  参考文献：
  名称：

  在温和条件下由催化量的活化剂诱导的自传播洛森重排

  摘要：

  已经开发了在中等至高极性有机溶剂中由催化量的活化剂引起的温和的自蔓延的洛森重排。在催化量（0.01当量）的乙酸酐和等摩尔量的碱（如干燥的碳酸钾）的存在下，芳族和脂族异羟肟酸的重排可以高收率得到相应的胺。传统Lossen重排的替代方法为从游离异羟肟酸合成胺提供了一种简单温和的方法。

  DOI：

  10.1016/j.tetlet.2014.12.084
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸甲酯 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以50%的产率得到2,6-dimethoxybenzohydroxamic acid
  参考文献：
  名称：

  碱介导的异羟肟酸的自我繁殖洛森重排，可有效而轻松地合成芳族和脂族伯胺†

  摘要：

  通过碱介导的重排将多种芳族和脂族异羟肟酸转化为相应的伯胺。这种重新排列可以少于1个当量进行。无需外部试剂的热条件下，在极性溶剂中分离K 2 CO 3。该重排具有几个特征，包括不需要用于促进重排的外部活化剂，少于一当量的碱足以进行该反应，以及其中仅产生二氧化碳作为副产物的清洁反应。提出了通过异氰酸酯中间体的自增长机理，并通过实验支持了基本的反应步骤，即链增长反应。

  DOI：

  10.1039/c6ob01178k

文献信息

• Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO–NHOH) to anilines
  作者：Yujiro Hoshino、Moriaki Okuno、Eri Kawamura、Kiyoshi Honda、Seiichi Inoue

  DOI：10.1039/b822806j

  日期：——

  Without using activating agents, a variety of free aromatic hydroxamic acids could be rearranged to aromatic amines in the presence of base alone.

  在不使用活化剂的情况下，可以在仅存在碱的情况下将多种游离的芳族异羟肟酸重排为芳族胺。
• Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions
  作者：Yujiro Hoshino、Yuki Shimbo、Naoya Ohtsuka、Kiyoshi Honda

  DOI：10.1016/j.tetlet.2014.12.084

  日期：2015.1

  self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields.

  已经开发了在中等至高极性有机溶剂中由催化量的活化剂引起的温和的自蔓延的洛森重排。在催化量（0.01当量）的乙酸酐和等摩尔量的碱（如干燥的碳酸钾）的存在下，芳族和脂族异羟肟酸的重排可以高收率得到相应的胺。传统Lossen重排的替代方法为从游离异羟肟酸合成胺提供了一种简单温和的方法。
• Benzohydroxamic acids as potent and selective anti-HCV agents
  作者：Maxim V. Kozlov、Alla A. Kleymenova、Lyudmila I. Romanova、Konstantin A. Konduktorov、Olga A. Smirnova、Vladimir S. Prasolov、Sergey N. Kochetkov

  DOI：10.1016/j.bmcl.2013.08.081

  日期：2013.11

  A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV. (C) 2013 Elsevier Ltd. All rights reserved.
• ——
  作者：Tyrone Woodard、Manik L. Debnath、Rupendra Simlot、Robert A. Izydore、Dwayne L. Daniels、Oi T. Wong、Hamby ElSourady、Iris H. Hall

  DOI：10.1023/a:1016226317975

  日期：——

  A series of 2-benzoyl-4,4-dialkyl-3,5-isoxazolidinediones proved to have potent hypolipidemic activity, lowering both serum cholesterol and triglyceride levels at 10 or 20 mg/kg/day, IP and orally in rodents. 2-(3,4,5-Trimethoxybenzoyl)-4,4-diethyl-3,5-isoxazolidinedione (4) afforded the best hypolipidemic activity lowering normolipidemic CF1 mouse serum cholesterol levels 49% and serum triglyceride levels 34% at 20 mg/kg/day, IP. Compound 4 was selected as a typical derivative of the chemical class for further detailed studies. Serum cholesterol levels in normolipidemic Sprague Dawley male rats were reduced 45% after 8 weeks at 10 and 20 mg/kg/day of compound, orally. Serum triglyceride levels were reduced 38-49% at 10 and 20 mg/kg/day, orally. In vitro liver enzyme activities studies in normolipidemic CF1 mice showed the compound inhibited mitochondrial citrate exchange, acetyl CoA synthetase, HMG CoA reductase, acyl CoA cholesterol acyl transferase, acetyl CoA carboxylase, sn-glycerol-3-phosphate acyl transferase, phosphatidylate phosphohydrolase and heparin-induced lipoprotein lipase activities with increases in the activities of cholesterol ester hydrolase and ATP-dependent citrate lyase. Similar enzyme activities were inhibited in vivo except HMG CoA reductase activity was not inhibited in rat liver or small intestinal mucosa after 8 weeks drug administration. Cholesterol levels were reduced in tissues after 8 weeks administration of compound 4 in normolipidemic rats. Bile cholesterol and triglyceride levels were elevated after two weeks administration to rats at 20 mg/kg/day. Serum lipoprotein levels in normolipidemic and hyperlipidemic rats showed the cholesterol levels in VLDL and LDL fractions after 4, 6 and 8 weeks at 10 and 20 mg/kg/day were reduced whereas HDL-cholesterol levels were significantly elevated. Studies demonstrated that H-3-cholesterol and C-14-palmitic acid incorporation into lipids of the lipoprotein fraction was reduced by the drug but P-32-incorporation was generally elevated. The agent demonstrated no observable toxicity in rats after 8 weeks administration, orally. The acute toxicity study in normolipidemic mice at 20, 40 and 100 mg/kg/day, IP, demonstrated no observable harmful effects of the drug.
• KONAJE A. C.; HOSANGADI B. D., INDIAN J. CHEM., 1979, B17, NO 3, 275-276
  作者：KONAJE A. C.、 HOSANGADI B. D.

  DOI：——

  日期：——