N-(3-hydroxy-4-methylphenyl)benzamide | 92199-49-0

• 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: N-(3-hydroxy-4-methylphenyl)benzamide
• 英文别名: N-(3-hydroxy-4-methyl-phenyl)-benzamide；4-Benzamino-2-hydroxy-toluol
• CAS: 92199-49-0
• 化学式: C₁₄H₁₃NO₂
• mdl: MFCD04151399
• 分子量: 227.263
• InChiKey: HOWNDUOBCWJDQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxy-4-methylphenyl)benzamide 在 四氯化碳 、 叔丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 8.0h， 生成 diethyl {2-hydroxy-3-methyl-6-[2-(trimethylsilyl)benzamido]phenyl}phosphonate
  参考文献：
  名称：

  σ ² P,O‐Hybrid Ligands: Synthesis of the First 4‐Hydroxy‐1,3‐benzazaphospholes by ortho ‐Lithiation of m ‐Amidophenyl Diethyl Phosphates

  摘要：

  AbstractThe m‐phosphorylanilides 2 are available from anilides 1 by the Atherton–Todd reaction; the selective ortho‐lithiation of the o′‐methyl‐protected phosphorylpivalanilide 2b with tBuLi proceeded in high yield in the presence of ClSiMe3. The ortho‐lithiation is followed by rapid 1,3‐migration of the PO3Et2 group to yield the phosphonoanilide cis/trans‐3b. This compound mainly reacts with excess LiAlH4 by reductive cyclization to form the 4‐hydroxy‐1H‐1,3‐benzazaphosphole 6. The lithiation of the o′‐unprotected phosphorylpivalanilide 2a with LDA was unselective and led to 3a and 4a in low yields, whereas additional ortho‐lithiation of the benzoyl group occurred for the lithiation of the o′‐protected phosphonobenzanilide 2c with tBuLi/LDA to give 7 in rather low yield. The reduction of crude 7 led to (benzylamino)phenol 8 and the 4‐hydroxy‐1H‐1,3‐benzazaphosphole 9 as a minor product. The properties, NMR spectroscopy data, and crystal structures of 5b, 6, and 8 are reported.

  DOI：

  10.1002/ejic.201402527
• 作为产物：
  描述：

  5-(Benzoylamino)-2-methylphenylbenzoate 在 甲醇 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 N-(3-hydroxy-4-methylphenyl)benzamide
  参考文献：
  名称：

  4-amino-thieno[3,2-c] pyridine-7-carboxylic acid derivatives

  摘要：

  本发明涉及公式化合物、含有它们的药物以及将这些化合物用作药用活性剂的用途。这些化合物表现出作为Raf激酶抑制剂的活性，因此可能对通过该激酶介导的疾病的治疗有用，特别是作为抗癌剂。

  公开号：

  US20070060607A1

文献信息

• Discovery of <i>meta</i>-Amido Bromophenols as New Antitubercular Agents
  作者：Jie Liang、Yun-xiang Tang、Xiang-zheng Tang、Hua-ju Liang、Yamin Gao、Cuiting Fang、Tian-yu Zhang、Ming Yan

  DOI：10.1248/cpb.c18-00917

  日期：2019.4.1

  Gram-positive and Gram-negative bacteria. Moderate cytotoxicities and good metabolic stability were observed for the selected compounds. The results demonstrated meta-amido bromophenols as a new class of antitubercular agents with good potentials.

  设计并合成了一系列间位氨基溴酚衍生物。发现该化合物有效抑制结核分枝杆菌H37Ra的生长。它们还显示出对结核分枝杆菌H37Rv和耐多药菌株的中等抑制活性。该化合物对正常的革兰氏阳性和革兰氏阴性细菌没有抑制活性。对于所选化合物，观察到中等的细胞毒性和良好的代谢稳定性。结果表明，间酰胺基溴酚是一类具有良好潜力的新型抗结核药。
• EPHA4 RTK INHIBITORS FOR TREATMENT OF NEUROLOGICAL AND NEURODEGENERATIVE DISORDERS AND CANCER
  申请人：Nantermet Philippe G.

  公开号：US20100197688A1

  公开（公告）日：2010-08-05

  The present invention is directed to compounds of generic formula (I) which are inhibitors of ephrin A4. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases regulated by the EphA4 RTK signaling, such as neurological and neurodegenerative disorders and cancer.

  本发明涉及通式（I）的化合物，这些化合物是ephrin A4的抑制剂。该发明还涉及包含这些化合物的药物组合物，以及在治疗由EphA4 RTK信号调节的疾病中使用这些化合物和组合物，例如神经系统和神经退行性疾病以及癌症。
• [EN] 2-(6-AMINO-PYRIDIN-3-YL)-2-HYDROXYETHYLAMINE DERIVATIVES AS BETA 2-ADRENOCEPTORS AGONISTS<br/>[FR] DERIVES DE 2-(6-AMINO-PYRIDINE-3-YL)-2-HYDROXYETHYLAMINE UTILISES COMME AGONISTES DES RECEPTEURS BETA 2-ADRENERGIQUES
  申请人：PFIZER LTD

  公开号：WO2004108676A1

  公开（公告）日：2004-12-16

  The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  该发明涉及公式（1）的化合物，以及用于制备、用于制备的中间体、含有和用途的过程。根据本发明的化合物在许多疾病、紊乱和状况中特别有用，特别是在炎症性、过敏性和呼吸系统疾病、紊乱和状况中。
• 2-(6-AMINO-PYRIDIN-3-YL)-2-HYDROXYETHYLAMINE DERIVATIVES AS BETA 2-ADRENOCEPTORS AGONISTS
  申请人：Pfizer Limited

  公开号：EP1633715A1

  公开（公告）日：2006-03-15
• 4-AMINO-THIENO[3,2-C]PYRIDINE-7-CARBOXYLIC ACID DERIVATIVES
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1926737A1

  公开（公告）日：2008-06-04