2-methoxy-5-nitro-1,3-benzenedicarboxylic acid | 140361-99-5

• 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-nitro-1,3-benzenedicarboxylic acid
• 英文别名: 2-methoxy-5-nitrobenzene-1,3-dicarboxylic acid
• CAS: 140361-99-5
• 化学式: C₉H₇NO₇
• 分子量: 241.157
• InChiKey: BQRGGXQUSINHOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  126.97
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-nitro-1,3-benzenedicarboxylic acid 在 吡啶 、 4-二甲氨基吡啶 、 (COCl₂)2 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 [(2R)-1-methoxypropan-2-yl] 2-[[2-methoxy-3-[[2-[(2R)-1-methoxypropan-2-yl]oxycarbonylphenyl]carbamoyl]-5-nitrobenzoyl]amino]benzoate
  参考文献：
  名称：

  基于2-甲氧基间苯二甲酰胺重复单元的一类新型的分子内氢键树突

  摘要：

  描述了基于2-甲氧基间苯二甲酰胺（2-OMe-IPA）重复单元的折叠树突的合成和构象性质。将通过2-甲氧基间苯二甲酰胺的顺式-顺式构象偏好预先组织的树枝状分子的流体力学性质与2,6-吡啶二甲酰胺（2,6-吡啶）类似物进行比较。通过1 H-DOSY NMR光谱和计算方法研究了2-OMe-IPA和2,6-pydic重复单元内存在的构象平衡性质的细微差异对相应树突的整体结构性质的影响。时间分辨荧光各向异性（TRFA）测量。而syn-syn2-OMe-IPA支链重复单元的优先选择完全通过分子内氢键相互作用来稳定，在2,6-pydic系统中的优先选择是分子内氢键和偶极子最小化效应的结果。但是，对于两个树突系列，非特异性的疏溶剂压缩在确定流体力学性质方面比在重复单元的构象平衡中依赖于溶剂的转变更为重要。

  DOI：

  10.1021/jo061351k
• 作为产物：
  描述：

  2,6-二甲基大茴香醚 在 potassium permanganate 、 硫酸 、 硝酸 作用下， 以 水 为溶剂， 生成 2-methoxy-5-nitro-1,3-benzenedicarboxylic acid
  参考文献：
  名称：

  基于2-甲氧基间苯二甲酰胺重复单元的一类新型的分子内氢键树突

  摘要：

  描述了基于2-甲氧基间苯二甲酰胺（2-OMe-IPA）重复单元的折叠树突的合成和构象性质。将通过2-甲氧基间苯二甲酰胺的顺式-顺式构象偏好预先组织的树枝状分子的流体力学性质与2,6-吡啶二甲酰胺（2,6-吡啶）类似物进行比较。通过1 H-DOSY NMR光谱和计算方法研究了2-OMe-IPA和2,6-pydic重复单元内存在的构象平衡性质的细微差异对相应树突的整体结构性质的影响。时间分辨荧光各向异性（TRFA）测量。而syn-syn2-OMe-IPA支链重复单元的优先选择完全通过分子内氢键相互作用来稳定，在2,6-pydic系统中的优先选择是分子内氢键和偶极子最小化效应的结果。但是，对于两个树突系列，非特异性的疏溶剂压缩在确定流体力学性质方面比在重复单元的构象平衡中依赖于溶剂的转变更为重要。

  DOI：

  10.1021/jo061351k

文献信息

• Synthesis of a New Mutagenic Benzoazepinoquinolinone Derivative
  作者：Tetsuya Kajimoto、Manabu Node、Minoru Ozeki、Atsushi Muroyama、Tetsushi Watanabe、Keiji Wakabayashi

  DOI：10.1055/s-0029-1217358

  日期：2009.7

  A novel mutagenic compound 1, isolated as a Maillard product trom tryptophan and glucose, was synthesized usmg Larock's quinoline formation, where addition ofiodonium cation to an acetylene moiety of N-propargylaniline triggers subsequent intramolecular electrophilic aromatic substitution to afford quinolines. The key synthetic intermediate 14 was obtained in a good yield when iodonium chloride was

  一种新的致突变化合物 1，作为美拉德产物从色氨酸和葡萄糖中分离出来，是利用 Larock 的喹啉形成合成的，其中碘鎓阳离子添加到 N-炔丙基苯胺的乙炔部分会触发随后的分子内亲电芳香取代以提供喹啉。以氯化碘为Larock法的引发剂，以良好的收率得到了关键的合成中间体14。14 与另外六个步骤的转换，包括内酰胺环的环化和 Curtius 重排，提供了目标分子 1。合成和分离的 1 在物理和光谱数据的比较中是相同的。
• Hydrogen Bonding-Directed Multicomponent Dynamic Covalent Assembly of Mono- and Bimacrocycles. Self-Sorting and Macrocycle Exchange
  作者：Jian-Bin Lin、Xiao-Na Xu、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1021/jo801972s

  日期：2008.12.5

  This paper describes the multicomponent dynamic covalent assembly of macrocyclic structures by utilizing hydrogen bonding-driven zigzag anthranilamides as "leading" components. Two or three amino groups have been introduced to one side of hydrogen bonded anthranilamide oligomers. The preorganization of the frameworks enabled the amino groups to condense with structurally matched aldehydes to form mono- and bimacrocycles in good to quantitative yields. Reactions from Lip to five components have been investigated. which involved one-step formation of up to six imine bonds. The preorganization of the templates highly enhanced the stability of the macrocyclic structures. As a result, all the macrocycles Could be purified by simply recrystallizing the Crude products from suitable solvents. Coexisting experiments of three series of three to five components were also performed, which all revealed that the preorganized precursors possessed high self-sorting capacity. On the basis of the same approach, a hydrazone-based macrocycle was also prepared quantitatively, while an intermacrocycle hydrazone-imine exchange was revealed to facilitate the formation of the hydrazone-based macrocycle from an imine-based macrocycle.
• Hydrogen-Bonding-Mediated Anthranilamide Homoduplexes. Increasing Stability through Preorganization and Iterative Arrangement of a Simple Amide Binding Site
  作者：Jiang Zhu、Jian-Bin Lin、Yun-Xiang Xu、Xue-Bin Shao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1021/ja064218i

  日期：2006.9.1

  This paper describes the assembly of two new series of self-complementary duplexes by making use of amide units, the simplest assembling units of hydrogen bonding, as binding sites. All the new monomers possess a rigidified anthranilamide skeleton, which is stabilized by intramolecular hydrogen bonding. Amide units are iteratively introduced to one side of the preorganized skeletons to facilitate the formation of intermolecular hydrogen bonding. Compounds 2 and 3 bear two and three CONH2 units, respectively, while 4, 6, and 7 are incorporated with two, three, and four AcNH units, respectively. For comparison, compound 5, which is similar to 4 but contains one AcNH and one CF3CONH unit, is also prepared. X-ray diffraction analysis of 2, 4, and 5 revealed homodimeric motifs in the solid state which are stabilized by two or more intermolecular hydrogen bonds. H-1 NMR investigations in CDCl3 indicated that all the compounds form hydrogen-bonded homoduplexes. Duplexes 3(.)3, 6(.)6, and 7(.)7 are highly stable in CDCl3, with a lower K-assoc limit of 2.3 x 10(5) M-1. The K-assoc values of the three duplexes in more polar CDCl3/CD3CN (9:1, v/v) were determined with the H-1 NMR dilution method. The result opens the way for the development of new polymeric duplexes of well-ordered structures.
• Chromogenic bis(urea) spherands: synthesis and complexation of lithium and sodium ions
  作者：Eddy Chapoteau、Manjit S. Chowdhary、Bronislaw P. Czech、Anand Kumar、Wolodymyr Zazulak

  DOI：10.1021/jo00036a009

  日期：1992.5

  Syntheses of two novel 18-membered bis(urea) spherands bearing 2,4,6-trinitroanilino and 4-(diethyl-amino)phenylazo chromophores are described. The UV-vis spectral changes in the presence and absence of Na+ and Li+ ions are reported at pH optima. Chromogenic spherand 2 exhibits selectivity for Na+ over Li+ in chloroform-water extractions. In contrast, Li+ ions are bound better than Na+ by both spherands in homogeneous aqueous media. The pK(a) values are determined for spherand 2 with Na+ and Li+ in 10% aqueous diethylene glycol monoethyl ether (DEGMEE). The extraction constants (K(ex)) for K+, Na+, and Li+ are determined for 2 in chloroform saturated with water, and the extraction selectivity order is Na+ > Li+ > K+.