3-[[hydroxy-[3-[[hydroxy-[3-[[hydroxy-(2-methoxy-5-methyl-3-nitrophenyl)methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-N-(2-methoxyphenyl)-5-methylbenzenecarboximidic acid | 923924-29-2

• 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: 3-[[hydroxy-[3-[[hydroxy-[3-[[hydroxy-(2-methoxy-5-methyl-3-nitrophenyl)methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-N-(2-methoxyphenyl)-5-methylbenzenecarboximidic acid
• CAS: 923924-29-2
• 化学式: C₄₃H₄₃N₅O₁₁
• 分子量: 805.841
• InChiKey: VBTURQCOCFMHDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  59
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  208
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-[[hydroxy-[3-[[hydroxy-[3-[[hydroxy-(2-methoxy-5-methyl-3-nitrophenyl)methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-N-(2-methoxyphenyl)-5-methylbenzenecarboximidic acid 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以35%的产率得到3-[[hydroxy-[3-[[hydroxy-[3-[[hydroxy-(2-hydroxy-5-methyl-3-nitrophenyl)methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-N-(2-methoxyphenyl)-5-methylbenzenecarboximidic acid
  参考文献：
  名称：

  Hydrogen Bonding-Induced Aromatic Oligoamide Foldamers as Spherand Analogues to Accelerate the Hydrolysis of Nitro-Substituted Anisole in Aqueous Media

  摘要：

  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.

  DOI：

  10.1021/jo0619940
• 作为产物：
  描述：

  2-methoxy-5-methyl-3-nitrobenzoic acid 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 氘代氯仿 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 3-[[hydroxy-[3-[[hydroxy-[3-[[hydroxy-(2-methoxy-5-methyl-3-nitrophenyl)methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-5-methylphenyl]methylidene]amino]-2-methoxy-N-(2-methoxyphenyl)-5-methylbenzenecarboximidic acid
  参考文献：
  名称：

  Hydrogen Bonding-Induced Aromatic Oligoamide Foldamers as Spherand Analogues to Accelerate the Hydrolysis of Nitro-Substituted Anisole in Aqueous Media

  摘要：

  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.

  DOI：

  10.1021/jo0619940

文献信息

• 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.