N-(2-azidoethyl)laurolactam | 1041381-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-(2-azidoethyl)laurolactam
• CAS: 1041381-42-3
• 化学式: C₁₄H₂₆N₄O
• 分子量: 266.387
• InChiKey: SQFHNUAZDWDFOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-azidoethyl)laurolactam 在 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 12a-N-((4-nitrophenyl)sulfonyl)-12a-azapentadecanelactam
  参考文献：
  名称：

  Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents

  摘要：

  Novel macrocyclic molecules comprising sulfonyl and acyl moiety at the position N-12a of 16-membered azalides (6a-n) and azalactams (10a-r) scaffold were synthesized from cyclododecanone 1 as starting material via 5 steps and 4 steps, respectively. The antifungal activity of these compounds against Sclerotinia sclerotiorum, Pyricularia oryzae, Botlytis cinerea, Rhizoctonia solani and Phytophthora capsici were evaluated and found that compounds possessing alpha-exomethylene (6c, 6d, 6e and 6g) showed antifungal activity comparable to commercial fungicide Chlorothalonil against P. oryzae and compounds possessing p-chlorobenzoyl exhibited enhanced antifungal activity than those with other substituents against S. sclerotiorum, P. oryzae, and B. cinerea. These findings suggested that the alpha-exomethylene and p-chlorobenzoyl may be two potential pharmacological active groups with antifungal activities. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.032
• 作为产物：
  描述：

  环十二酮 在 sodium azide 、 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 N-(2-azidoethyl)laurolactam
  参考文献：
  名称：

  Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents

  摘要：

  Novel macrocyclic molecules comprising sulfonyl and acyl moiety at the position N-12a of 16-membered azalides (6a-n) and azalactams (10a-r) scaffold were synthesized from cyclododecanone 1 as starting material via 5 steps and 4 steps, respectively. The antifungal activity of these compounds against Sclerotinia sclerotiorum, Pyricularia oryzae, Botlytis cinerea, Rhizoctonia solani and Phytophthora capsici were evaluated and found that compounds possessing alpha-exomethylene (6c, 6d, 6e and 6g) showed antifungal activity comparable to commercial fungicide Chlorothalonil against P. oryzae and compounds possessing p-chlorobenzoyl exhibited enhanced antifungal activity than those with other substituents against S. sclerotiorum, P. oryzae, and B. cinerea. These findings suggested that the alpha-exomethylene and p-chlorobenzoyl may be two potential pharmacological active groups with antifungal activities. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.032

文献信息

• Design, Synthesis, and Fungicidal Activity of Macrolactones and Macrolactams with a Sulfonamide Side Chain
  作者：Wei-Juan Zhu、Peng Wu、Xiao-Mei Liang、Yan-Hong Dong、Jian-Jun Zhang、Hui-Zu Yuan、Shu-Hua Qi、Xiang-Qing Meng、Jin-Ping Wu、Fu-Heng Chen、Dao-Quan Wang

  DOI：10.1021/jf800796z

  日期：2008.8.1

  Four series of novel macrolactones and macrolactams-12-alkylsulfonamido-1,15-pentadecanlactones (5), 12-alkylsulfonamido-15-methyl-1,15-pentadecanlactones (6), 12-alkylsulfonamido-1,15-pentadecanlactams (7), and N-(alkylsulfonamidoethyl)-l, 1 2-dodecanlactams (8)-were designed and synthesized from readily available 2-nitrocyclododecanone or cyclodoclecanone. Their structures were confirmed by 1H NIVIR, IR, and elemental analysis. The bioassay showed that these compounds displayed fair to excellent fungicidal activity against Rhizoctonia solani KOhn and have a gradual increase of fungicidal activity in the order of 6, 7, 8, and 5. Among them, compounds 5a, 5b, and 5c displayed excellent fungicidal activity against R. solani comparable with the commercial fungicide carbendazim. Above results illustrated that the rule on the relationship between the activity and hydrogen-bonding, namely the macrocyclic compounds with a hydrogen-bonding acceptor and a hydrogen-bonding donor on the ring and having a three methylenes distance between two polarizable groups have the best fungicidal activity against R. solani, has a general suitability to the macrocyclic compounds, and pesticide molecules may combine with a target enzyme by hydrogen-bonding. The facts, which compound 6 has a much lower fungicidal activity against R. solani than compound 5 but their diff erence in chemical structure is only that there is a methyl group on the C15 for compound 6 and none but hydrogen atom on the C15 for compound 5, indicated that a methyl group plays an inhibitory role to the fungicidal activity. It suggests that the existence of a methyl group with a great volume between two polarizable groups would interfere in the interaction of pesticide molecules and the target enzyme.