tert-butyloxycarbonyl-12a-azapentadecanelactone | 1568982-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: tert-butyloxycarbonyl-12a-azapentadecanelactone
• CAS: 1568982-39-7
• 化学式: C₁₉H₃₅NO₄
• 分子量: 341.491
• InChiKey: XZYMEHLCLRAOIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyloxycarbonyl-12a-azapentadecanelactone 在 盐酸 、 potassium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 12a-N-((3-nitrophenyl)sulfonyl)-2-methylene-12a-azapentadecanelactone
  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：

  二碳酸二叔丁酯 、 1-oxa-4-azacyclohexadecan-16-one 以 水 为溶剂， 以98%的产率得到tert-butyloxycarbonyl-12a-azapentadecanelactone
  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