2-(4-Bromophenyl)imino-17-oxa-1-thia-3,4-diazaspiro[4.15]icos-3-en-16-one | 1021189-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(4-Bromophenyl)imino-17-oxa-1-thia-3,4-diazaspiro[4.15]icos-3-en-16-one
• CAS: 1021189-57-0
• 化学式: C₂₂H₃₀BrN₃O₂S
• 分子量: 480.469
• InChiKey: QUCAMEYFDGNCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到2-(4-Bromophenyl)imino-17-oxa-1-thia-3,4-diazaspiro[4.15]icos-3-en-16-one
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Structure−Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings

  摘要：

  Two series of novel spiro-compounds containing macrolactam or macrolactone and thiadiazoline rings, 1-thia-2-alkylimino-3,4,9-triaza-10-oxospiro[4.15]eicosyl-3-ene (4F) and 1-thia-2-alkylimino-3,4-diaza-9-oxa-10-oxospiro[4.15]eicosyl-3-ene (4G), were synthesized from 12-oxo-1,15-pentade-caniactam and 12-oxo-1,15-pentadecanlactone, respectively. Their structures were confirmed by elemental analysis, H-1 NMR, and C-13 NMR. The conformation of compounds 4F was determined via the crystal structure of a representative compound (4F(6)). The bioassay showed that compounds 4F have much better fungicidal activity against five fungi (Botrytis cinerea Pers., Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn., Phomopsis asparagi Sacc., and Pyricularia oryzae Cav.) than compounds 4G. The fact above showed that the presence of a hydrogen-bonding donor for the fungicidal activity of macrocyclic compounds is very important. 4F6 showed excellent fungicidal activity against P. oryzae, which is much better than the commercial fungicide isoprothiolane, and 4F(13) showed excellent fungicidal activity against P. oryzae and good fungicidal activity against P. asparagi.

  DOI：

  10.1021/jf903665f