N-(2-bromophenyl)-2-oxocyclohexylsulfonamide | 925234-61-3

• 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-(2-bromophenyl)-2-oxocyclohexylsulfonamide
• 英文别名: N-(2-bromophenyl)-2-oxocyclohexane-1-sulfonamide
• CAS: 925234-61-3
• 化学式: C₁₂H₁₄BrNO₃S
• 分子量: 332.218
• InChiKey: XNLQEQHLWFMGRL-UHFFFAOYSA-N

物化性质

• 沸点：
  463.2±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-bromophenyl)-2-oxocyclohexylsulfonamide 在 氨 、 titanium(IV)isopropoxide 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、5.33 kPa 条件下， 反应 8.0h， 生成
  参考文献：
  名称：

  一种环己烷并噻二嗪化合物及其制备方法与应用

  摘要：

  本发明属于农用化学品技术领域，本发明公开了一种环己烷并噻二嗪化合物及其制备方法与应用。本发明合成得到新的环己烷并噻二嗪系列化合物，经生物活性测定结果表明所合成的化合物具有良好的杀菌活性，本发明所得环己烷并噻二嗪化合物在抑制油菜菌核、番茄灰霉、水稻纹枯、水稻稻瘟和禾谷镰刀中具有很好的应用效果，适宜大范围的推广应用。

  公开号：

  CN114685398B
• 作为产物：
  描述：

  环己酮 在 草酰氯 、 sulfur trioxide dioxane complex 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 N-(2-bromophenyl)-2-oxocyclohexylsulfonamide
  参考文献：
  名称：

  一种环己烷并噻二嗪化合物及其制备方法与应用

  摘要：

  本发明属于农用化学品技术领域，本发明公开了一种环己烷并噻二嗪化合物及其制备方法与应用。本发明合成得到新的环己烷并噻二嗪系列化合物，经生物活性测定结果表明所合成的化合物具有良好的杀菌活性，本发明所得环己烷并噻二嗪化合物在抑制油菜菌核、番茄灰霉、水稻纹枯、水稻稻瘟和禾谷镰刀中具有很好的应用效果，适宜大范围的推广应用。

  公开号：

  CN114685398B

文献信息

• Synthesis and biological activities of 2-oxocycloalkylsulfonamides
  作者：Xinghai Li、Xinling Yang、Xiaomei Liang、Zhenpeng Kai、Huizu Yuan、Dekai Yuan、Jianjun Zhang、Ruiqing Wang、Fuxiang Ran、Shuhua Qi、Yun Ling、Fuheng Chen、Daoquan Wang

  DOI：10.1016/j.bmc.2008.02.048

  日期：2008.4

  A series of novel 2-oxocycloalkylsulfonamides ( 4) were synthesized and their structures confirmed by IR, H-1 NMR, and elemental analysis. The bioassay showed that they have fair to excellent fungicidal activities against Botrytis cinerea Pers and Sclerotinia sclerotiorum. Among them, compounds 4A(10), 4A(11), 4A(12), 4B(2), and 4B(3), the EC50 values of which were 2.12, 3.66, 3.96, 2.38, and 2.43 mu g/mL, respectively, displayed excellent fungicidal activity against B. cinerea Pers, and are comparable with commercial fungicide procymidone ( the EC50 value is 2.45 mu g/mL). 3D QSAR against B. cinerea Pers was studied, a statistically significant and chemically meaningful CoMFA model was developed and some compounds which have a high predicted activity were forecasted. In addition, the bioassay also showed that the compounds have good inhibitory activities against human tumor cells HL-60, BGC-823, Bel-7402 and KB. It is interesting to point out that the antitumor activities of compounds 4 are in accordance with their fungicidal activity to a great extent: compounds having relatively best antitumor activities ( 4A10, 4A11, 4A12, and 4B3) also displayed excellent fungicidal activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides
  作者：Xing-Hai Li、De-Cai Wu、Zhi-Qiu Qi、Xiu-Wei Li、Zu-Min Gu、Song-Hong Wei、Yang Zhang、Ying-Zi Wang、Ming-Shan Ji

  DOI：10.1021/jf102348x

  日期：2010.11.10

  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.
• Novel sulfonamides against Botrytis cinerea with no positive cross-resistance to commercial fungicides: Design, synthesis and SAR study
  作者：Nan Cai、Lu He、Kai Wang、Zhihui Feng、Zining Cui、Mingshan Ji、Zhiqiu Qi、Peiwen Qin、Xinghai Li

  DOI：10.1016/j.bmcl.2019.126859

  日期：2020.2

  Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by H-1 NMR, C-13 NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.
• 一种环己烷并噻二嗪化合物及其制备方法与应用
  申请人：沈阳农业大学

  公开号：CN114685398B

  公开（公告）日：2023-04-18

  本发明属于农用化学品技术领域，本发明公开了一种环己烷并噻二嗪化合物及其制备方法与应用。本发明合成得到新的环己烷并噻二嗪系列化合物，经生物活性测定结果表明所合成的化合物具有良好的杀菌活性，本发明所得环己烷并噻二嗪化合物在抑制油菜菌核、番茄灰霉、水稻纹枯、水稻稻瘟和禾谷镰刀中具有很好的应用效果，适宜大范围的推广应用。