(13E)-13-[(2-chloro-6-fluorophenyl)methoxyimino]-azacyclopentadecan-2-one | 1003852-49-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (13E)-13-[(2-chloro-6-fluorophenyl)methoxyimino]-azacyclopentadecan-2-one
• CAS: 1003852-49-0
• 化学式: C₂₁H₃₀ClFN₂O₂
• 分子量: 396.933
• InChiKey: FWNBOUXIDQPHIJ-KOEQRZSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  12-oxotetradecano-14-lactam 、 O-[(2-氯-6-氟苯基)甲基]羟胺盐酸盐 在 吡啶 作用下， 反应 16.0h， 生成 (13Z)-13-[(2-chloro-6-fluorophenyl)methoxyimino]-azacyclopentadecan-2-one 、 (13E)-13-[(2-chloro-6-fluorophenyl)methoxyimino]-azacyclopentadecan-2-one
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Macrolactams and Macrolactones with an Oxime Ether Side Chain

  摘要：

  Three series of novel macrolactams and macrolactones - 12-alkoxyimino-tetradecanlactam, 12-alkoxyiminopentadecanlactam, and 12-alkoxyiminodecanlactone derivatives (7A, 7B, and 7C) - were synthesized from corresponding 12-oxomacrolactams and 12-oxomacrolactone. Their structures were confirmed by H-1 NMR and elemental analysis. The Z and E isomers of 7A and 7B were separated, and their configurations were determined by H-1 NMR. These compounds showed fair to excellent fungicidal activities against Rhizoctonia solani Kuhn. It is interesting that the Z and E isomers of most of the compounds have quite different fungicidal activities. The fact that the compounds have a gradual increase of fungicidal activity in the order of 7A, 7C, and 7B indicated that the macrocyclic derivatives with a hydrogen-bonding acceptor (=N-O-) and a hydrogen-bonding donor (-CONH-) on the ring, and a three methylenes distance (CH2CH2CH2) between these two functional groups, exhibited the best fungicidal activity. The bioassay also showed that 7B not only has good fungicidal activity but also may have a broad spectrum of fungicidal activities.

  DOI：

  10.1021/jf072733+