N-[4-chloro-2-(trifluoromethyl)phenyl]-2-oxocyclopentane-1-sulfonamide | 1253692-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-chloro-2-(trifluoromethyl)phenyl]-2-oxocyclopentane-1-sulfonamide
• CAS: 1253692-11-3
• 化学式: C₁₂H₁₁ClF₃NO₃S
• 分子量: 341.738
• InChiKey: LMMXKEXFNJMNTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[4-chloro-2-(trifluoromethyl)phenyl]-2-oxocyclopentane-1-sulfonamide 在 sodium tetrahydroborate 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以78%的产率得到N-[4-chloro-2-(trifluoromethyl)phenyl]-2-hydroxycyclopentane-1-sulfonamide
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides

  摘要：

  To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by H-1 nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC50 values of the compounds 3C, 4C, 3D, and 40 were 0.80, 0.85, 1.22, and 1.09 mu g/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC50 values of compounds 3A, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 mu g/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.

  DOI：

  10.1021/jf102348x
• 作为产物：
  描述：

  环戊酮 在 草酰氯 、 sulfur trioxide dioxane complex 作用下， 生成 N-[4-chloro-2-(trifluoromethyl)phenyl]-2-oxocyclopentane-1-sulfonamide
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides

  摘要：

  To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by H-1 nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC50 values of the compounds 3C, 4C, 3D, and 40 were 0.80, 0.85, 1.22, and 1.09 mu g/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC50 values of compounds 3A, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 mu g/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.

  DOI：

  10.1021/jf102348x

文献信息

• Design, synthesis and fungicidal activity of novel 2-substituted aminocycloalkylsulfonamides
  作者：Caixiu Liu、Xiaojing Yan、Minlong Wang、Peiwen Qin、Zhiqiu Qi、Mingshan Ji、Xingyu Liu、P. Vijaya Babu、Xinghai Li、Zi-Ning Cui

  DOI：10.1016/j.bmcl.2016.11.061

  日期：2017.1

  III29, III30 and III31 showed excellent fungicidal activity against a strain of B. cinerea (CY-09), with EC50 values of 3.17, 3.04, 2.54 and 1.99 mg/L respectively. Their in vivo fungicidal activities were also better than the positive controls cyprodinil, procymidone, boscalid and carbendazim in pot experiments. Moreover, the fungicidal activity of III28 (EC50 = 4.62 mg/L) against P. grisea was also

  通过高选择性的N-烷基化反应，设计合成了一系列新颖的2-取代的氨基环烷基磺酰胺，其结构经1 H NMR，13 C NMR和HRMS表征。其中，化合物III12和III20的构型通过X射线单晶衍射确认。生物测定表明，标题化合物对灰葡萄孢和稻瘟病菌的不同菌株具有相当大的作用。与阳性对照嘧啶酮（EC 50  = 10.31 mg / L）相比，化合物III28，III29，III30和III31对灰葡萄孢菌株（CY-09）表现出优异的杀真菌活性，EC 50值分别为3.17、3.04、2.54和1.99 mg / L。在盆栽实验中，它们的体内杀真菌活性也优于阳性对照环丙啶，丙咪唑，卡斯卡利和多菌灵。此外，III28（EC 50  = 4.62 mg / L）对稻瘟病菌的杀真菌活性也好于阳性对照异硫杂环戊烷（EC 50  = 6.11 mg / L）。基于结构-活性关系，化合物III28作为有望成为