4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime O-2''propenyl ether | 1206846-12-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime O-2''propenyl ether
• 英文别名: (Z,E)-N-prop-2-enoxy-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-imine
• CAS: 1206846-12-9
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: DMJXQQCOZVACOA-BBFBKMQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-buten-2'-ketoxime 、 3-溴丙烯 在 sodium hydride 、 二甲基亚砜 作用下， 反应 2.0h， 生成 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime O-2''propenyl ether 、 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(E)-ketoxime O-2''propenyl ether
  参考文献：
  名称：

  Antifungal Activity of 4′-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3′-butene-2′-ketoximeN-O-Alkyl Ethers

  摘要：

  A number of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-alkyl ethers were prepared, separated into their E and Z isomers, and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro for antifungal activity against four important phytopathogenic fungi, namely, Sclerotium rolfsii, Rhizoctonia bataticola, Macrophomina phaseolina, and Sclerotinia sclerotiorum. E isomers of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-propyl ether (ED50 = 32.36 mu g mL(-1)) and 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-(1 ''-methyl) ethyl ether (ED50 = 35.50 mu g mL(-1)) showed maximum antifungal activity against R. bataticola and S. rolfsii, respectively, whereas 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether was found to be active against M. phaseolina (ED50 = 31.08 mu g mL(-1)) and S. sclerotiorum (ED50 21.39 mu g mL(-1)), respectively. The Z isomer of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-pentyl ether, which was found to be most effective, was tested against S. sclerotiorum in a greenhouse at 1 and 5% concentrations. The 5% aqueous emulsion of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether suppressed disease development in pea by 90-95% as compared with the untreated infested soil in the greenhouse after 21 days of treatment.

  DOI：

  10.1021/jf903044j

文献信息

• Antifungal Activity of 4′-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3′-butene-2′-ketoxime<i>N</i>-<i>O</i>-Alkyl Ethers
  作者：Tirthankar Banerjee、Prem Dureja

  DOI：10.1021/jf903044j

  日期：2010.1.27

  A number of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-alkyl ethers were prepared, separated into their E and Z isomers, and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro for antifungal activity against four important phytopathogenic fungi, namely, Sclerotium rolfsii, Rhizoctonia bataticola, Macrophomina phaseolina, and Sclerotinia sclerotiorum. E isomers of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-propyl ether (ED50 = 32.36 mu g mL(-1)) and 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-(1 ''-methyl) ethyl ether (ED50 = 35.50 mu g mL(-1)) showed maximum antifungal activity against R. bataticola and S. rolfsii, respectively, whereas 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether was found to be active against M. phaseolina (ED50 = 31.08 mu g mL(-1)) and S. sclerotiorum (ED50 21.39 mu g mL(-1)), respectively. The Z isomer of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-pentyl ether, which was found to be most effective, was tested against S. sclerotiorum in a greenhouse at 1 and 5% concentrations. The 5% aqueous emulsion of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether suppressed disease development in pea by 90-95% as compared with the untreated infested soil in the greenhouse after 21 days of treatment.