5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide | 860032-69-5

• 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: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide
• 英文别名: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholin-4-ylmethyl)benzamide
• CAS: 860032-69-5
• 化学式: C₁₈H₁₇Cl₂N₃O₅
• 分子量: 426.256
• InChiKey: HGDLVZWHMLSPBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide 以 甲苯 为溶剂， 反应 8.0h， 生成 6-chloro-N-(2-chloro-4-nitrophenyl)-3,4-dihydro-3-[(4-nitrophenyl)methylene]-2-oxo-2H-1-benzopyran-8-carboxamide
  参考文献：
  名称：

  Chemistry of Phosphorus Ylides. Part 22 [1]. Effect of Newly Synthesized Niclosamide Mannich Bases, Phosphopyranones, Phosphoranylidenes, and Oxaphosphinin on Some Metabolic Aspects of Biomphalaria Alexandrina

  摘要：

  Niclosamide reacts with secondary amines and formaldehyde under the condition of Mannich reaction, to give new Mannich bases. The reaction of these niclosamide Mannich bases with active phosphacumulene ylides affords the corresponding phenyliminopyranone, pyranone, and pyranthione, respectively. When Wittig reaction was carried out on the pyranone, using p-nitrobenzaldehyde, a new arylidene and triphenylphosphine oxide were obtained. On the other hand, stabilized phosphonium ylides affect the transylidation of niclosamide Mannich bases to the corresponding phosphoranylidenes. When diphenylmethylenetriphenylphosphorane reacts with a niclosamide Mannich base, an oxaphosphinin was obtained. The molluscicidal potency of the newly synthesized derivatives against Biomphalaria alexandrina was studied, too.

  DOI：

  10.1007/s00706-004-0226-2
• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 氯硝柳胺 以 乙醇 、 水 为溶剂， 以95%的产率得到5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide
  参考文献：
  名称：

  磷化氢的化学。第25部分[1]。六苯基碳二磷烷与羰基，和 曼尼希 碱的相互作用 。磷酰亚烷基，磷酸甜菜碱和草酰膦的合成

  摘要：

  烯丙基六苯基碳二膦烷与羰基的反应得到相应的亚磷叉基衍生物。另一方面，当使双膦烷与α-二酮和三酮反应时，获得稳定的磷酸甜菜碱。从双膦烷与的反应中分离出氮杂膦亚基。此外，双膦烷与烟酰胺和喹啉 曼尼希 碱反应 形成氧代膦。当用新的 膦烷进行维蒂希 反应时，获得了相应的环外烯烃。另一方面，当在 霍夫曼 降解反应条件下处理膦烷时，产生草酰膦 。

  DOI：

  10.1007/s00706-007-0843-7

文献信息

• Synthesis of Phosphonodithioate, Oxathiaphosphinin, Oxathiaphosphole, and Dithiaphosphole Derivatives from the Reaction of Lawesson's Reagent with Phenolic Mannich Bases and Oxime Derivatives
  作者：Soher S. Maigali、Fouad M. Soliman、Rashad Shabana、Marwa El-Hussieny

  DOI：10.1080/10426500802487607

  日期：2009.9.18

  The reaction of Lawesson's reagent 1a, with niclosamide 2 proceeded by thionation and formation of carbothioamide 3 and the zwitterionic oxathiaphosphinin 4a. LR reacted with 8-hydroxyquinoline (5), 2-methylquinoline-4-ol (7), and β-naphthol (9) to give the phosphonodithioates 6, 8, or 10. The reaction of LR with the Mannich bases 11 and 14 afforded the oxathiaphosphinins 13 and 15, whereas the phosphonodithioates

  Lawesson 试剂 1a 与氯硝柳胺 2 的反应通过硫代化并形成硫代酰胺 3 和两性离子氧硫杂膦 4a 进行。LR 与 8-羟基喹啉 (5)、2-甲基喹啉-4-醇 (7) 和 β-萘酚 (9) 反应生成二硫代膦酸 6、8 或 10。 LR 与曼尼希碱 11 和 14 的反应得到氧硫杂膦 13 和 15，而在曼尼希碱 16 和 18 的情况下分离出二硫代膦酰基酯 17 和 19。LR 与邻苯二甲酰亚胺曼尼希碱 20 反应得到二硫酮 21 和 N-甲基邻苯二甲酰亚胺 (22)。酮单肟 23 与 LR 的反应导致形成氧硫杂磷 24 和二硫杂磷 25，而单肟 26 得到硫代乙酮硫肟 27。酮二肟 28 和 34 分别得到二硫代膦酸 29 和 36
• Chemistry of phosphorus ylides. Part 25 [1]. Interaction of hexaphenylcarbodiphosphorane with carbonyls, hydrazone, and Mannich bases. A synthesis of phosphoranylidenes, phosphobetaines, and oxaphosphinin
  作者：Medhat M. Said、Soher S. Maigali、Mansoura A. Abd-El-Maksoud、Fouad M. Soliman

  DOI：10.1007/s00706-007-0843-7

  日期：2008.11

  reacted with niclosamide and quinoline Mannich bases with the formation of the oxaphosphinins. When the Wittig reaction was performed with the new phosphoranes, the corresponding exocyclic olefins were obtained. On the other hand, the oxaphosphinins were produced when the phosphoranes were treated under the condition of a Hoffmann degradation reaction.

  烯丙基六苯基碳二膦烷与羰基的反应得到相应的亚磷叉基衍生物。另一方面，当使双膦烷与α-二酮和三酮反应时，获得稳定的磷酸甜菜碱。从双膦烷与的反应中分离出氮杂膦亚基。此外，双膦烷与烟酰胺和喹啉 曼尼希 碱反应 形成氧代膦。当用新的 膦烷进行维蒂希 反应时，获得了相应的环外烯烃。另一方面，当在 霍夫曼 降解反应条件下处理膦烷时，产生草酰膦 。
• Chemistry of Phosphorus Ylides. Part 22 [1]. Effect of Newly Synthesized Niclosamide Mannich Bases, Phosphopyranones, Phosphoranylidenes, and Oxaphosphinin on Some Metabolic Aspects of Biomphalaria Alexandrina
  作者：Fouad M. Soliman、Medhat M. Said、Soher S. Maigali

  DOI：10.1007/s00706-004-0226-2

  日期：2005.2

  Niclosamide reacts with secondary amines and formaldehyde under the condition of Mannich reaction, to give new Mannich bases. The reaction of these niclosamide Mannich bases with active phosphacumulene ylides affords the corresponding phenyliminopyranone, pyranone, and pyranthione, respectively. When Wittig reaction was carried out on the pyranone, using p-nitrobenzaldehyde, a new arylidene and triphenylphosphine oxide were obtained. On the other hand, stabilized phosphonium ylides affect the transylidation of niclosamide Mannich bases to the corresponding phosphoranylidenes. When diphenylmethylenetriphenylphosphorane reacts with a niclosamide Mannich base, an oxaphosphinin was obtained. The molluscicidal potency of the newly synthesized derivatives against Biomphalaria alexandrina was studied, too.