N-(2-甲氧基苯基)-2-(吗啉-4-羰基)-5-硝基苯甲酰胺 | 1025775-00-1

• 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: N-(2-甲氧基苯基)-2-(吗啉-4-羰基)-5-硝基苯甲酰胺
• 英文名称: N-(2-methoxyphenyl)-2-(morpholine-4-carbonyl)-5-nitrobenzamide
• CAS: 1025775-00-1
• 化学式: C₁₉H₁₉N₃O₆
• 分子量: 385.376
• InChiKey: XIXPTAFIUKKZTM-UHFFFAOYSA-N

物化性质

• 沸点：
  554.7±50.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-甲氧基苯基)-2-(吗啉-4-羰基)-5-硝基苯甲酰胺 在 sodium hydroxide 、 水 作用下， 以 乙腈 为溶剂， 生成 吗啉 、 2-((2-甲氧基苯基)氨基甲酰基)-5-硝基苯甲酸 、 2-((2-甲氧基苯基)氨基甲酰基)-4-硝基苯甲酸
  参考文献：
  名称：

  动力学和大型率提高的机制在碱性水解N'吗啉代ñ - （2'-甲氧基苯基）邻苯二

  摘要：

  The apparent second-order rate constant (k(OH)) for hydroxide-ion-catalyzed conversion of 1 to N-(2'-methoxyphenyl)phthalamate (4) is similar to 10(3)-fold larger than k(OH) for alkaline hydrolysis of N-morpholinobenzamide (2). These results are explained in terms of the reaction scheme 1 -> 3 -> 4 where 3 represents N-(2'-methoxyphenyl)phthalimide and the values of k(2obs)/k(1obs) Vary from 6.0 x 10(2) to 17 x 10(2) within [NaOH] range of 5.0 x 10(-3) to 2.0 M. Pseudo-first-order rate constants (k(obs)) for alkaline hydrolysis of 1 decrease from 21.7 x 10(-3) to 15.6 x 10(-3) s(-1) with an increase in ionic strength (by NaCl) from 0.5 to 2.5 M at 0.5 M NaOH and 35 degrees C. The values of k(obs), obtained for alkaline hydrolysis of 2 within [NaOH] range 1.0 x 10(-2) to 2.0 M at 35 degrees C, follow the relationship k(obs) = k(OH)[HO-] + k(OH)'[HO-](2) with least-squares calculated values of k(OH) and k(OH)' as (6.38 +/- 0.15) x 10(-5) and (4.59 +/- 0.09) x 10(-5) M-2 s(-1), respectively. A few kinetic runs for aqueous cleavage of 1, N'-morpholino-N-(2'-methoxyphenyl)-5-nitrophthalamide (5) and N'-morpholino-N-(2'-methoxyphenyt)-4-nitrophthalamide (6) at 35 degrees C and 0.05 M NaOH as well as 0.05 M NaOD reveal the solvent deuterium kinetic isotope effect (= k(obs)(H2O)/k(obs)(D2O)) as 1.6 for 1, 1.9 for 5, and 1.8 for 6. Product characterization study on the cleavage of 5, 6, and N-(2'-methoxyphenyl)-4-nitrophthalimide (7) at 0.5 M NaOD in D2O solvent shows the imide-intermediate mechanism as the exclusive mechanism.

  DOI：

  10.1021/jo702695k
• 作为产物：
  描述：

  吗啉 、 N-(2-methoxyphenyl)-4-nitrophthalimide 以 四氢呋喃 为溶剂， 反应 17.0h， 以101 mg的产率得到N-(2-甲氧基苯基)-2-(吗啉-4-羰基)-5-硝基苯甲酰胺
  参考文献：
  名称：

  动力学和大型率提高的机制在碱性水解N'吗啉代ñ - （2'-甲氧基苯基）邻苯二

  摘要：

  The apparent second-order rate constant (k(OH)) for hydroxide-ion-catalyzed conversion of 1 to N-(2'-methoxyphenyl)phthalamate (4) is similar to 10(3)-fold larger than k(OH) for alkaline hydrolysis of N-morpholinobenzamide (2). These results are explained in terms of the reaction scheme 1 -> 3 -> 4 where 3 represents N-(2'-methoxyphenyl)phthalimide and the values of k(2obs)/k(1obs) Vary from 6.0 x 10(2) to 17 x 10(2) within [NaOH] range of 5.0 x 10(-3) to 2.0 M. Pseudo-first-order rate constants (k(obs)) for alkaline hydrolysis of 1 decrease from 21.7 x 10(-3) to 15.6 x 10(-3) s(-1) with an increase in ionic strength (by NaCl) from 0.5 to 2.5 M at 0.5 M NaOH and 35 degrees C. The values of k(obs), obtained for alkaline hydrolysis of 2 within [NaOH] range 1.0 x 10(-2) to 2.0 M at 35 degrees C, follow the relationship k(obs) = k(OH)[HO-] + k(OH)'[HO-](2) with least-squares calculated values of k(OH) and k(OH)' as (6.38 +/- 0.15) x 10(-5) and (4.59 +/- 0.09) x 10(-5) M-2 s(-1), respectively. A few kinetic runs for aqueous cleavage of 1, N'-morpholino-N-(2'-methoxyphenyl)-5-nitrophthalamide (5) and N'-morpholino-N-(2'-methoxyphenyt)-4-nitrophthalamide (6) at 35 degrees C and 0.05 M NaOH as well as 0.05 M NaOD reveal the solvent deuterium kinetic isotope effect (= k(obs)(H2O)/k(obs)(D2O)) as 1.6 for 1, 1.9 for 5, and 1.8 for 6. Product characterization study on the cleavage of 5, 6, and N-(2'-methoxyphenyl)-4-nitrophthalimide (7) at 0.5 M NaOD in D2O solvent shows the imide-intermediate mechanism as the exclusive mechanism.

  DOI：

  10.1021/jo702695k