2-methoxy-5-methyl-3-nitrobenzoic acid | 858848-07-4

• 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-methoxy-5-methyl-3-nitrobenzoic acid
• CAS: 858848-07-4
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: KJPNRXSFTKTXSH-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  389.9±42.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-methyl-3-nitrobenzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-Methoxy-5-methyl-3-nitro-benzoyl chloride
  参考文献：
  名称：

  构象稳定的芳香族低聚酰胺的合成、结构研究、氢-氘交换研究和分子建模

  摘要：

  通过在内部放置分子内氢键来偏置芳香低聚酰胺的构象偏好，导致了一系列稳定折叠的分子链。本文介绍了对这些折叠低聚物的广泛固态、溶液和计算研究的结果。根据其骨架长度，低聚酰胺采用新月形或螺旋形构象。令人惊讶的是，尽管主链具有高度重复的性质，但如氢-氘交换数据所示，内部放置的、否则非常相似的分子内氢键显示出显着不同的稳定性。还观察到氢键强度可以通过调整连接到芳族骨架外部的取代基来调节。检查三聚体的酰胺氢-氘交换率表明，靠近酯端的六元氢键是分子的所有四个分子内氢键中最弱的。这一观察结果通过 B3LYP/6-31G* 水平的从头算量子力学计算得到了验证。这样的“弱点”创造了主链扭曲集中的“凸起之战”，这在所研究的四个三聚体分子的固态结构中一致观察到。在固态下，低聚物组装成有趣的一维结构。观察到短寡聚体（即二聚体、三聚体和四聚体）的明显柱状堆积和较长寡聚体（即四聚体、五聚体和六聚体）的通道状、潜在的离子传导堆叠。

  DOI：

  10.1021/ja100579z
• 作为产物：
  描述：

  5-甲基水杨酸甲酯 在 sodium hydroxide 、 18-冠醚-6 、 硝酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 63.0h， 生成 2-methoxy-5-methyl-3-nitrobenzoic acid
  参考文献：
  名称：

  Hydrogen-bonding-induced oligoanthranilamide foldamers. Synthesis, characterization, and complexation for aliphatic ammonium ions

  摘要：

  The self-assembly of a novel series of intramolecular hydrogen bonding-driven foldamers have been described. Five linear aromatic amide oligomers 1-5, which bear two to six repeating benzoyl amide subunits, respectively, have been prepared by continuous amide-coupling reactions. The existence of three-centered hydrogen bonds in the oligomers and consequently, the folding conformation of the oligomers in the solid state and solution have been proved by the X-ray analysis (for 2) and the H-1 NMR and IR experiments. Molecular modeling reveals a planar and rigid conformation for the oligomers and a cavity of 0.86 nm in diameter for 6-mer 5. Fluorescent and H-1 NMR experiments have demonstrated that the new aromatic oligo-amide foldamers can bind primary and secondary alkyl ammonium ions in chloroform and the associated binding constants have been determined. It is revealed that 5-mer 4 exhibits the largest binding ability. A face-to-face binding mode has been proposed for the complexes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.042

文献信息

• Highly selective one-pot synthesis of H-bonded pentagon-shaped circular aromatic pentamers
  作者：Bo Qin、Wei Qiang Ong、Ruijuan Ye、Zhiyun Du、Xiuying Chen、Yan Yan、Kun Zhang、Haibin Su、Huaqiang Zeng

  DOI：10.1039/c0cc05791f

  日期：——

  One-pot, multi-molecular macrocyclization allows the highly selective preparation of pentagon-shaped circular aromatic pentamers mediated by an inward-pointing continuous hydrogen-bonding network.

  一锅法多分子大环化反应可通过内向连续氢键网络介导高选择性制备五边形环形芳香五聚体。
• Helical Organization in Foldable Aromatic Oligoamides by a Continuous Hydrogen-Bonding Network
  作者：Yan Yan、Bo Qin、Yingying Shu、Xiuying Chen、Yeow Kwan Yip、Dawei Zhang、Haibin Su、Huaqiang Zeng

  DOI：10.1021/ol802679p

  日期：2009.3.19

  Introduction of a continuous internal hydrogen-bonding network suppressed the conformational flexibility of a series of oligoaromatic foldamers; with a lengthened backbone. The helical ordering over up to six aromatic repeating units was established in solution by a 2D NOESY study and in the solid state by an X-ray diffraction method. Computational molecular modeling further corroborates the experimentally observed helical propagation in this class of foldable molecular strands.
• Hydrogen Bonding-Induced Aromatic Oligoamide Foldamers as Spherand Analogues to Accelerate the Hydrolysis of Nitro-Substituted Anisole in Aqueous Media
  作者：Hui-Ping Yi、Jiang Wu、Kui-Ling Ding、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1021/jo0619940

  日期：2007.2.1

  Four intramolecular hydrogen bonding-driven aromatic amide foldamers 2-5 have been designed and synthesized in which a 2-methoxy-3-nitrobenzamide unit was incorporated at the end of the backbone. Kinetic studies in dioxane-water (4:1, v/v) at 60-90 degrees C have revealed that the folded backbone of the oligomers was, like the rigidified spherand, able to complex Li+, Na+, and K+ and, consequently, accelerated the hydrolysis of the nitro-appended anisole unit of the foldamers. Generally, longer foldamers displayed an increased accelerating effect, and LiOH displayed the highest reactivity probably due to the most efficient complexation by the folded oligomers. Addition of excessive potassium chloride substantially reduced the complexing interaction, and the hydrolysis of the longer oligomers became slower than that of the shorter ones due to an increased steric effect. The results indicate that, even in a hot aqueous medium of high polarity, intramolecular hydrogen bonding is still able to induce structurally matched oligomers to generate a preorganized rigidified conformation.
• Hydrogen-bonding-induced oligoanthranilamide foldamers. Synthesis, characterization, and complexation for aliphatic ammonium ions
  作者：Hui-Ping Yi、Chuang Li、Jun-Li Hou、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2005.06.042

  日期：2005.8

  The self-assembly of a novel series of intramolecular hydrogen bonding-driven foldamers have been described. Five linear aromatic amide oligomers 1-5, which bear two to six repeating benzoyl amide subunits, respectively, have been prepared by continuous amide-coupling reactions. The existence of three-centered hydrogen bonds in the oligomers and consequently, the folding conformation of the oligomers in the solid state and solution have been proved by the X-ray analysis (for 2) and the H-1 NMR and IR experiments. Molecular modeling reveals a planar and rigid conformation for the oligomers and a cavity of 0.86 nm in diameter for 6-mer 5. Fluorescent and H-1 NMR experiments have demonstrated that the new aromatic oligo-amide foldamers can bind primary and secondary alkyl ammonium ions in chloroform and the associated binding constants have been determined. It is revealed that 5-mer 4 exhibits the largest binding ability. A face-to-face binding mode has been proposed for the complexes. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis, Structural Investigations, Hydrogen−Deuterium Exchange Studies, and Molecular Modeling of Conformationally Stablilized Aromatic Oligoamides
  作者：Yan Yan、Bo Qin、Changliang Ren、Xiuying Chen、Yeow Kwan Yip、Ruijuan Ye、Dawei Zhang、Haibin Su、Huaqiang Zeng

  DOI：10.1021/ja100579z

  日期：2010.4.28

  Biasing the conformational preferences of aromatic oligoamides by internally placing intramolecular hydrogen bonds has led to a series of stably folded molecular strands. This article presents the results from extensive solid-state, solution, and computational studies on these folding oligomers. Depending on its backbone length, an oligoamide adopts a crescent or helical conformation. Surprisingly, despite

  通过在内部放置分子内氢键来偏置芳香低聚酰胺的构象偏好，导致了一系列稳定折叠的分子链。本文介绍了对这些折叠低聚物的广泛固态、溶液和计算研究的结果。根据其骨架长度，低聚酰胺采用新月形或螺旋形构象。令人惊讶的是，尽管主链具有高度重复的性质，但如氢-氘交换数据所示，内部放置的、否则非常相似的分子内氢键显示出显着不同的稳定性。还观察到氢键强度可以通过调整连接到芳族骨架外部的取代基来调节。检查三聚体的酰胺氢-氘交换率表明，靠近酯端的六元氢键是分子的所有四个分子内氢键中最弱的。这一观察结果通过 B3LYP/6-31G* 水平的从头算量子力学计算得到了验证。这样的“弱点”创造了主链扭曲集中的“凸起之战”，这在所研究的四个三聚体分子的固态结构中一致观察到。在固态下，低聚物组装成有趣的一维结构。观察到短寡聚体（即二聚体、三聚体和四聚体）的明显柱状堆积和较长寡聚体（即四聚体、五聚体和六聚体）的通道状、潜在的离子传导堆叠。