2-氟-N-(2-羟基-4-甲基苯基)苯甲酰胺 | 564446-18-0

• 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: 2-氟-N-(2-羟基-4-甲基苯基)苯甲酰胺
• 英文名称: 2-fluoro-N-(2-hydroxy-4-methylphenyl)-benzamide
• 英文别名: 2-fluoro-N-(2-hydroxy-4-methylphenyl)benzamide
• CAS: 564446-18-0
• 化学式: C₁₄H₁₂FNO₂
• mdl: MFCD04486817
• 分子量: 245.253
• InChiKey: BDBQVSKABQTQKD-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  305.2±42.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟-N-(2-羟基-4-甲基苯基)苯甲酰胺 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-methyl-dibenzo[b,f][1,4]oxazepin-11(10H)-one
  参考文献：
  名称：

  接力有机光氧化还原/N-杂环卡宾催化不对称合成二苯并恶氮并吡咯烷酮

  摘要：

  通过光氧化还原/ N-杂环卡宾 (NHC) 中继催化，实现了前所未有的高度立体选择性合成吡咯并 [1,2- d ][1,4]oxazep​​in-3(2 H )-ones。有机光氧化还原催化促进胺氧化生成亚胺，然后进行 NHC 催化的 [3 + 2] 环化反应，以实现优异的非对映和对映选择性二苯并恶氮杂合吡咯烷酮。

  DOI：

  10.1021/acs.orglett.3c00685
• 作为产物：
  描述：

  邻氟苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-氟-N-(2-羟基-4-甲基苯基)苯甲酰胺
  参考文献：
  名称：

  Characterization of the Histamine H₄ Receptor Binding Site. Part 1. Synthesis and Pharmacological Evaluation of Dibenzodiazepine Derivatives

  摘要：

  A series of dibenzodiazepine derivatives was synthesized to probe the binding site of the recently discovered histamine H-4 receptor (H4R). Optimization of the lead structure clozapine (2) resulted in (E)-7-chloro-11-(4-methylpiperazin-l-yl) dibenzo[b, f][1,4] oxazepine (7j), a potent H4R agonist (H4R, pK(i) = 7.6). Pharmacological data suggests that the series of nonimidazole compounds can be used to describe the orthosteric binding site of the H4R because both 2 and 7j displace [H-3] histamine in a competitive manner. Furthermore, it is demonstrated that the effects of 7j are competitively antagonized by the selective H4R antagonist JNJ 7777120 (1), indicating considerable overlap of their binding sites. On the basis of the derived structure-activity relationships and additional pharmacological results, a pharmacophore model was constructed, which will be the premise for the design of novel H4R ligands.

  DOI：

  10.1021/jm051008s

文献信息

• Characterization of the Histamine H₄ Receptor Binding Site. Part 1. Synthesis and Pharmacological Evaluation of Dibenzodiazepine Derivatives
  作者：Rogier A. Smits、Herman D. Lim、Bart Stegink、Remko A. Bakker、Iwan J. P. de Esch、Rob Leurs

  DOI：10.1021/jm051008s

  日期：2006.7.1

  A series of dibenzodiazepine derivatives was synthesized to probe the binding site of the recently discovered histamine H-4 receptor (H4R). Optimization of the lead structure clozapine (2) resulted in (E)-7-chloro-11-(4-methylpiperazin-l-yl) dibenzo[b, f][1,4] oxazepine (7j), a potent H4R agonist (H4R, pK(i) = 7.6). Pharmacological data suggests that the series of nonimidazole compounds can be used to describe the orthosteric binding site of the H4R because both 2 and 7j displace [H-3] histamine in a competitive manner. Furthermore, it is demonstrated that the effects of 7j are competitively antagonized by the selective H4R antagonist JNJ 7777120 (1), indicating considerable overlap of their binding sites. On the basis of the derived structure-activity relationships and additional pharmacological results, a pharmacophore model was constructed, which will be the premise for the design of novel H4R ligands.
• Relay Organophotoredox/<i>N</i>-Heterocyclic Carbene Catalysis-Enabled Asymmetric Synthesis of Dibenzoxazepine-Fused Pyrrolidinones
  作者：Yaseen Hussain、Deepak Sharma、Tamanna、Pankaj Chauhan

  DOI：10.1021/acs.orglett.3c00685

  日期：2023.4.14

  An unprecedented highly stereoselective synthesis of pyrrolo[1,2-d][1,4]oxazepin-3(2H)-ones has been accomplished via photoredox/N-heterocyclic carbene (NHC) relay catalysis. A wide range of substituted dibenzoxazepines and aryl/hetereoaryl enals were well accommodated under the organic photoredox catalysis-promoted amine oxidation to generate the imines, followed by a NHC-catalyzed [3 + 2] annulation

  通过光氧化还原/ N-杂环卡宾 (NHC) 中继催化，实现了前所未有的高度立体选择性合成吡咯并 [1,2- d ][1,4]oxazep​​in-3(2 H )-ones。有机光氧化还原催化促进胺氧化生成亚胺，然后进行 NHC 催化的 [3 + 2] 环化反应，以实现优异的非对映和对映选择性二苯并恶氮杂合吡咯烷酮。