2',4'-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1'-biphenyl]-3-carboxamide | 1058742-44-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2',4'-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1'-biphenyl]-3-carboxamide
• 英文别名: 2',4'-Difluoro-3-{[4-nitro-3-(trifluoromethyl)phenyl]carbamoyl}[1,1'-biphenyl]-4-yl 4-chlorobenzoate；[4-(2,4-difluorophenyl)-2-[[4-nitro-3-(trifluoromethyl)phenyl]carbamoyl]phenyl] 4-chlorobenzoate
• CAS: 1058742-44-1
• 化学式: C₂₇H₁₄ClF₅N₂O₅
• 分子量: 576.864
• InChiKey: OQEFCNSFNBSYHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  二氟尼柳 在 氯化亚砜 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 19.0h， 生成 2',4'-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1'-biphenyl]-3-carboxamide
  参考文献：
  名称：

  Synthesis and Crystal Structure of Two Diflunisal Carboxamides

  摘要：

  标题化合物，2′,4′-二氟-4-[(4-甲基苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2a和2′,4′-二氟-4-[(4-氯苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2b，是通过对羧酸的酰胺化和对酚羟基的酯化反应从已注册的抗炎药物双氟尼沙尔合成的，并经过丁酮-乙醇重结晶，已通过单晶X射线衍射确认[CCDC 753735和753736]。化合物2a在三斜空间组Pī中结晶，单元参数为a = 10.562(2) Å，b = 10.696(2) Å，c = 11.061(2) Å，α = 80.503(7)°，β = 84.722(7)°，γ = 73.553(7)°，Z = 2。化合物2b在三斜空间组Pī中结晶，单元参数为a = 9.348(3) Å，b = 11.150(3) Å，c = 11.798(4) Å，α = 106.627(4)°，β = 93.223(4)°，γ = 91.579(5)°，Z = 2。它们的堆积通过分子间N–H···O氢键得到稳定。标题化合物2′,4′-二氟-4-[(4-甲基苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2a和2′,4′-二氟-4-[(4-氯苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2b，经过酰胺化和酯化反应确认了分子间氢键的稳定性。

  DOI：

  10.1007/s10870-010-9728-4

文献信息

• Synthesis and Crystal Structure of Two Diflunisal Carboxamides
  作者：Guang-xiang Zhong、Hong-dan Hu、Chun-nian Xia、Jian-song Jiang、Ting-ting Chen

  DOI：10.1007/s10870-010-9728-4

  日期：2010.9

  The title compounds, 2′,4′-difluoro-4-[(4-methylbenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl) phenyl]-[1,1′-biphenyl]-3-carboxamide 2a and 2′,4′-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1′-biphenyl]-3-carboxamide 2b, synthesized from diflunisal, a registered anti-inflammatory drug, via amidation of carboxlic acid and esterification of phenolic hydroxy group and recrystallized from butanone-ethanol, were confirmed by single-crystal X-ray diffraction [CCDC 753735 and 753736]. The 2a crystallizes in triclinic space group Pī with cell parameters a = 10.562(2) Å, b = 10.696(2) Å, c = 11.061(2) Å, α = 80.503(7)°, β = 84.722(7)°, γ = 73.553(7)° and Z = 2. The 2b crystallizes in triclinic space group Pī with cell parameters a = 9.348(3) Å, b = 11.150(3) Å, c = 11.798(4) Å, α = 106.627(4)°, β = 93.223(4)°, γ = 91.579(5)° and Z = 2. Their packing are stabilized by intermolecular N–H···O hydrogen bonds. The title compounds, 2′,4′-difluoro-4-[(4-methylbenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl)phenyl]-[1,1′-biphenyl]-3-carboxamide 2a and 2′,4′-difluoro-4-[(4-chlorobenzoyl)oxy]-N-[4-nitro-3-(trifluoromethyl) phenyl]-[1,1′-biphenyl]-3-carboxamide 2b, synthesized from diflunisal, a registered anti-inflammatory drug, via amidation of carboxlic acid and esterification of phenolic hydroxy group, were confirmed by single- crystal X-ray diffraction showing their packing are stabilized by intermolecular hydrogen bonds .

  标题化合物，2′,4′-二氟-4-[(4-甲基苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2a和2′,4′-二氟-4-[(4-氯苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2b，是通过对羧酸的酰胺化和对酚羟基的酯化反应从已注册的抗炎药物双氟尼沙尔合成的，并经过丁酮-乙醇重结晶，已通过单晶X射线衍射确认[CCDC 753735和753736]。化合物2a在三斜空间组Pī中结晶，单元参数为a = 10.562(2) Å，b = 10.696(2) Å，c = 11.061(2) Å，α = 80.503(7)°，β = 84.722(7)°，γ = 73.553(7)°，Z = 2。化合物2b在三斜空间组Pī中结晶，单元参数为a = 9.348(3) Å，b = 11.150(3) Å，c = 11.798(4) Å，α = 106.627(4)°，β = 93.223(4)°，γ = 91.579(5)°，Z = 2。它们的堆积通过分子间N–H···O氢键得到稳定。标题化合物2′,4′-二氟-4-[(4-甲基苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2a和2′,4′-二氟-4-[(4-氯苯甲酰)氧]-N-[4-硝基-3-(三氟甲基)苯]-[1,1′-联苯]-3-羧酰胺2b，经过酰胺化和酯化反应确认了分子间氢键的稳定性。