4-氨基甲酰基-3-碘苯甲酸 | 857088-45-0

• 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: 4-氨基甲酰基-3-碘苯甲酸
• 英文名称: 4-(aminocarbonyl)-3-iodobenzoic acid
• 英文别名: 3-iodoterephthalamic acid；4-Carbamoyl-3-iodobenzoic acid
• CAS: 857088-45-0
• 化学式: C₈H₆INO₃
• 分子量: 291.045
• InChiKey: DQLKCCDZCPIDOR-UHFFFAOYSA-N

物化性质

• 沸点：
  420.7±40.0 °C(Predicted)
• 密度：
  2.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基甲酰基-3-碘苯甲酸 在 双氧水 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 4.33h， 生成 3-diphenylphosphoryl-4-(aminocarbonyl)benzoic acid
  参考文献：
  名称：

  Rapid and Selective Nitroxyl (HNO) Trapping by Phosphines: Kinetics and New Aqueous Ligations for HNO Detection and Quantitation

  摘要：

  Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (center dot NO), but the lack of HNO detection methods limits the understanding its in vivo mechanisms and the identification of endogenous sources. We previously demonstrated that reaction of HNO with triarylphosphines provides aza-ylides and HNO-derived amides, which may serve as stable HNO biomarkers. We now report a kinetic analysis for the trapping of HNO by phosphines, ligations of enzyme-generated HNO, and compatibility studies illustrating the selectivity of phosphines for HNO over other physiologically relevant nitrogen oxides. Quantification of HNO using phosphines is demonstrated using an HPLC-based assay and ligations of phosphine carbamates generate HNO-derived ureas. These results further demonstrate the potential of phosphine probes for reliable biological detection and quantification of HNO.

  DOI：

  10.1021/ja203652z
• 作为产物：
  描述：

  2-氨基对苯二甲酸甲酯 在 ammonium hydroxide 、 亚硝酸特丁酯 、 三氟乙酸 、 sodium iodide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 12.0h， 生成 4-氨基甲酰基-3-碘苯甲酸
  参考文献：
  名称：

  新型的α，α-二氟邻苯二甲酰亚胺通过铜催化的2-卤代苯甲酰胺与α，α-二氟Reformatskii试剂的交叉偶联环化

  摘要：

  新颖α，α-difluorohomophthalimides 2通过反应制备ñ -取代2-卤代苯甲酰胺与α，α-二氟Reformatskii试剂BrZnCF 2 CO 2的Et（3）中的CuBr的在室温下的存在。合成过程涉及CuBr介导的3与芳基碘化物或活化的芳基溴化物的交叉偶联，然后在室温下自生环化2-苯甲酰胺基-α，α-二氟乙酸乙酯中间体。还通过使3当量的3进行反应，制备了带有能够充当羧酸生物等排体的酸性酰亚胺质子的N-未取代的α，α-二氟邻苯二甲酰亚胺2（R'= H）。与母体2-碘苯甲酰胺。其他芳基碘化物，例如3-碘-咪唑并[1,2-α]吡啶也用于串联偶联-环化反应。

  DOI：

  10.1021/jo050599r

文献信息

• Novel α,α-Difluorohomophthalimides via Copper-Catalyzed Tandom Cross-Coupling−Cyclization of 2-Halobenzamides with α,α-Difluoro Reformatskii Reagent
  作者：Yijun Pan、Christopher P. Holmes、David Tumelty

  DOI：10.1021/jo050599r

  日期：2005.6.1

  Novel α,α-difluorohomophthalimides 2 were prepared by reacting N-substituted 2-halobenzamides with the α,α-difluoro Reformatskii reagent BrZnCF2CO2Et (3) in the presence of CuBr at room temperature. The synthesis involves a CuBr-mediated cross-coupling of 3 with aryl iodides or activated aryl bromides, followed by a spontaneous cyclization of the ethyl 2-benzamido-α,α-difluoroacetate intermediates

  新颖α，α-difluorohomophthalimides 2通过反应制备ñ -取代2-卤代苯甲酰胺与α，α-二氟Reformatskii试剂BrZnCF 2 CO 2的Et（3）中的CuBr的在室温下的存在。合成过程涉及CuBr介导的3与芳基碘化物或活化的芳基溴化物的交叉偶联，然后在室温下自生环化2-苯甲酰胺基-α，α-二氟乙酸乙酯中间体。还通过使3当量的3进行反应，制备了带有能够充当羧酸生物等排体的酸性酰亚胺质子的N-未取代的α，α-二氟邻苯二甲酰亚胺2（R'= H）。与母体2-碘苯甲酰胺。其他芳基碘化物，例如3-碘-咪唑并[1,2-α]吡啶也用于串联偶联-环化反应。
• Rapid and Selective Nitroxyl (HNO) Trapping by Phosphines: Kinetics and New Aqueous Ligations for HNO Detection and Quantitation
  作者：Julie A. Reisz、Charles N. Zink、S. Bruce King

  DOI：10.1021/ja203652z

  日期：2011.8.3

  Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (center dot NO), but the lack of HNO detection methods limits the understanding its in vivo mechanisms and the identification of endogenous sources. We previously demonstrated that reaction of HNO with triarylphosphines provides aza-ylides and HNO-derived amides, which may serve as stable HNO biomarkers. We now report a kinetic analysis for the trapping of HNO by phosphines, ligations of enzyme-generated HNO, and compatibility studies illustrating the selectivity of phosphines for HNO over other physiologically relevant nitrogen oxides. Quantification of HNO using phosphines is demonstrated using an HPLC-based assay and ligations of phosphine carbamates generate HNO-derived ureas. These results further demonstrate the potential of phosphine probes for reliable biological detection and quantification of HNO.