N-(3-甲氧基苄基)-3-(三氟甲基)苯甲酰胺 | 1002439-86-2

• 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: N-(3-甲氧基苄基)-3-(三氟甲基)苯甲酰胺
• 英文名称: N-[(3-methoxyphenyl)methyl]-3-(trifluoromethyl)benzamide
• 英文别名: N-(3-methoxybenzyl)-3-(trifluoromethyl)benzamide
• CAS: 1002439-86-2
• 化学式: C₁₆H₁₄F₃NO₂
• 分子量: 309.288
• InChiKey: ZMMDRJWLSMVEEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-三氟甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(3-甲氧基苄基)-3-(三氟甲基)苯甲酰胺
  参考文献：
  名称：

  Design and synthesis of 3-aminophthalazine derivatives and structural analogues as PDE5 inhibitors: anti-allodynic effect against neuropathic pain in a mouse model

  摘要：

  Neuropathic pain is a chronic pain caused by a lesion or disease affecting the somatosensory nervous system. To date, no specific treatment has been developed to cure this pain. Antidepressants and anticonvulsant drugs are used, but they do not demonstrate universal efficacy, and they often cause detrimental adverse effects. Some studies highlighted the efficacy of sildenafil, a well-known inhibitor of phosphodiesterase 5 (PDE5, (IC50=3.3 nM)), in models of pain. Based on these results, we focused our attention on MY 5445, another known PDE5 inhibitor. Homologues, isosteres and structural analogues of MY 5445 were designed and all synthesized compounds were evaluated for their inhibitory activity toward PDE5. Selectivity profiles towards other PDE1-4 isoenzymes, water solubility and stability in acidic medium of the most potent PDE5 inhibitors were determined and the aminophthalazine 16h and its mimetic 41n (3-aminoindazole) were evaluated in comparison to MY 5445 (4b) in vivo in a model of neuropathic pain induced by sciatic nerve cuffing in mice (3 and 0.5 mg/kg, ip twice a day). Both compounds showed the same efficacy on neuropathic allodynia as MY 5445, and thus produced a significant relief of mechanical hypersensitivity after 12 days of treatment. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.026

文献信息

• Palladium-catalyzed regio- and chemoselective ortho-benzylation of C–H bond using a functionalizable primary amide directing group: a concise synthesis of dibenzo[b,e]azepin-6-ones
  作者：Joydev K. Laha、Pooja U. Shah、Krupal P. Jethava

  DOI：10.1039/c3cc43835j

  日期：——

  A palladium-catalyzed regio- and chemoselective direct benzylation of primary benzamides with 2-bromobenzyl bromides under a mild basic condition has been developed affording various substituted diarylmethanes in good yields. Furthermore, the directing amide group (–CONH2) was subjected to intramolecular N-arylation with the aryl bromide moiety present in diarylmethanes leading to a concise synthesis of dibenzoazepinones.

  开发了一种在温和碱性条件下，使用氯化钯催化的原料苯甲酰胺与2溴苄基溴的区域和化学选择性直接苄基化反应，能够以良好的产率合成多种取代二芳基甲烷。此外，导向酰胺基团 (–CONH2) 还与二芳基甲烷中存在的芳基溴部分进行了分子内N-芳基化反应，从而实现了二苄基氨基酮的简洁合成。