N-benzyl-3-methoxysalicylamide | 29327-85-3

• 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-benzyl-3-methoxysalicylamide
• 英文别名: N-benzyl-2-hydroxy-3-methoxybenzamide
• CAS: 29327-85-3
• 化学式: C₁₅H₁₅NO₃
• mdl: MFCD08850677
• 分子量: 257.289
• InChiKey: ADWXMLRCMVEIBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  433.8±45.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-methoxysalicylamide 在 高氯酸 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Synthesis and study of new photochromic unsymmetrical bis-spiropyrans with nonequivalent heteroarene fragments conjugated through the common 2H,8H-pyrano[2,3-f]chromene moiety

  摘要：

  DOI：

  10.1016/j.molstruc.2020.128808
• 作为产物：
  描述：

  3-甲氧基水杨酸 、 苄胺 在 三氯化磷 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以33%的产率得到N-benzyl-3-methoxysalicylamide
  参考文献：
  名称：

  On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides

  摘要：

  六十六种在酰基部位3、4或5以及苄芳香环上的位置4处取代的N-苄基水杨酰胺被合成。这些化合物被测试其对结核分枝杆菌、堪萨斯分枝杆菌和埃维分枝杆菌的体外抗结核活性。为了评估结构-抗结核活性关系（QSARs），采用了基于Free-Wilson方法以及Free-Wilson和Hansch方法的组合方法（取代基常数用于描述苄基取代基的影响，指示参数用于酰基部位的取代基）。对于苄基取代基，使用Hammett常数对于QSAR方程并不重要。脂溶性参数（π^2）的二次表示仅在抗结核活性对埃维分枝杆菌的QSAR方程中显著。

  DOI：

  10.1135/cccc20031275

文献信息

• On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides
  作者：Karel Waisser、Milan Peřina、Věra Klimešová、Jarmila Kaustová

  DOI：10.1135/cccc20031275

  日期：——

  Sixty-six N-benzylsalicylamides substituted in the acyl moiety in positions 3, 4 or 5 and in position 4 on the benzylic aromatic ring were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. To evaluate structure-antimycobacterial activity relationships (QSARs), approaches based on the Free-Wilson as well as a combination of the Free-Wilson and Hansch methods were employed (substituent constants were used to describe the influence of the benzyl substituents, indicator parameters were used for the substituents on the acyl moiety). The use of the Hammett constants for benzyl substituents was not important for QSAR equations. The quadratic representation of lipophilicity parameters (π²) was significant only in QSAR equations of antimycobacterial activity against M. avium.

  六十六种在酰基部位3、4或5以及苄芳香环上的位置4处取代的N-苄基水杨酰胺被合成。这些化合物被测试其对结核分枝杆菌、堪萨斯分枝杆菌和埃维分枝杆菌的体外抗结核活性。为了评估结构-抗结核活性关系（QSARs），采用了基于Free-Wilson方法以及Free-Wilson和Hansch方法的组合方法（取代基常数用于描述苄基取代基的影响，指示参数用于酰基部位的取代基）。对于苄基取代基，使用Hammett常数对于QSAR方程并不重要。脂溶性参数（π^2）的二次表示仅在抗结核活性对埃维分枝杆菌的QSAR方程中显著。
• 3-Benzyl-2H-1,3-benzoxazine-2,4(3H)-diones, a new group of antimycobacterial compounds against potentially pathogenic strains
  作者：Karel Waisser、Milan Peřina、Jiřı́ Kuneš、Vera Klimešová、Jarmila Kaustová

  DOI：10.1016/j.farmac.2003.07.004

  日期：2003.11

  A series of derivatives of 3-benzyl-2H-benzoxazine-2,4(3H)-dione substituted in positions 6, 7 or 8 on the benzoxazine, and in positions 3 or 4 on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium avium and two strains of Mycobacterium kansasii. The disadvantage of the compounds is in their low solubility in water. The antimycobacterial activity of N-benzylsalicylamides correlates with that of 3-benzyl-2H-1,3-benzoxazin-2,4(3H)-diones and depends on the partition coefficients and electronic indexes.
• Synthesis and study of new photochromic unsymmetrical bis-spiropyrans with nonequivalent heteroarene fragments conjugated through the common 2H,8H-pyrano[2,3-f]chromene moiety
  作者：Ilya V. Ozhogin、Eugene L. Mukhanov、Anatoly V. Chernyshev、Artem D. Pugachev、Boris S. Lukyanov、Anatoly V. Metelitsa

  DOI：10.1016/j.molstruc.2020.128808

  日期：2020.12