13-aza-1,15-cyclopentadecanolide fluoroborate | 950583-85-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 13-aza-1,15-cyclopentadecanolide fluoroborate
• 英文别名: 12a-azapentadecanelactone tetrafluoroborate；1-oxa-4-azacyclohexadecan-16-one tetrafluoroborate；1-Oxa-4-azoniacyclohexadecan-16-one;tetrafluoroborate；1-oxa-4-azoniacyclohexadecan-16-one;tetrafluoroborate
• CAS: 950583-85-4
• 化学式: BF₄*C₁₄H₂₇NO₂*H
• 分子量: 329.186
• InChiKey: ZVDDBGVDLFKJNH-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  42.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  13-aza-1,15-cyclopentadecanolide fluoroborate 在 水 、 sodium carbonate 作用下， 生成 1-oxa-4-azacyclohexadecan-16-one
  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：

  2-叠氮基乙醇 、 环十二酮 在 三氟化硼乙醚 作用下， 反应 12.0h， 以85%的产率得到13-aza-1,15-cyclopentadecanolide fluoroborate
  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

• Primary Study on Mode of Action for Macrocyclic Fungicide Candidates (<b>7B3</b>, <b>D1</b>) against Rhizoctonia solani Kühn
  作者：Xiaojing Yan、Xiaomei Liang、Shuhui Jin、Jinping Lv、Chunxin Yu、Wenyan Qi、Baoju Li、Huizhu Yuan、Shuhua Qi、Yanxia Shi、Jingping Wu、Fuheng Chen、Daoquan Wang

  DOI：10.1021/jf9037369

  日期：2010.3.10

  A novel macrolactam fungicide candidate (7B3) and a novel aza-macrolactone fungicide candidate (D1) were designed and synthesized, and the bioassay showed that both displayed excellent fungicidal activity against Rhizoctonia solani Kuhn. To elucidate the biochemical mode of action of the two compounds against R. solani and illustrate the similarities and differences of action mechanism resulting from subtle differences in structure of the two compounds, the effects of the two compounds on the ultrastructure of hyphae, electrolyte leakage, and respiration of mycelia cell suspension caused by 7B3 or D1 were studied. The results showed that the two compounds had very similar modes of action. Both induced irregular swelling of hyphae, vacuolation of cytoplasm, and thickening of cell wall. The conductivity of mycelia cell suspension increased in the presence of 7B3 or D1, which indicated that the two compounds had a similar effect on cell membrane permeability. In addition, both 7B3 and D1 were insufficient in inhibiting the respiration of mycelia.
• Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents
  作者：Xiaolei Wang、Shun Zhang、Yanlong Pang、Huihui Yuan、Xiaomei Liang、Jianjun Zhang、Daoquan Wang、Mingan Wang、Yanhong Dong

  DOI：10.1016/j.ejmech.2013.11.032

  日期：2014.2

  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.