4-chloro-N-(16-oxo-oxacyclohexadec-5-yl)benzenesulfonamide | 1020841-68-2

• 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: 4-chloro-N-(16-oxo-oxacyclohexadec-5-yl)benzenesulfonamide
• CAS: 1020841-68-2
• 化学式: C₂₁H₃₂ClNO₄S
• 分子量: 430.008
• InChiKey: ZTFMPPZRMBYDMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  13-amino-oxacyclohexadecan-2-one;hydrochloride 、 4-氯苯磺酰氯 在 吡啶 作用下， 以 乙腈 为溶剂， 以40%的产率得到4-chloro-N-(16-oxo-oxacyclohexadec-5-yl)benzenesulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Fungicidal Activity of Macrolactones and Macrolactams with a Sulfonamide Side Chain

  摘要：

  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.

  DOI：

  10.1021/jf800796z

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.