(-)-1-[(1R)-nopyl]-3-methylimidazolium chloride

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-1-[(1R)-nopyl]-3-methylimidazolium chloride
• 英文别名: 1-[2-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]ethyl]-3-methylimidazol-3-ium;chloride
• 化学式: C₁₅H₂₃N₂*Cl
• 分子量: 266.814
• InChiKey: QYGXQIFTFSEJCJ-IODNYQNNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-1-[(1R)-nopyl]-3-methylimidazolium chloride 、 D-扁桃酸 在 sodium 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到(-)-1-[(1R)-nopyl]-3-methylimidazolium (R)-mandelate
  参考文献：
  名称：

  Synthesis and Phytotoxicity of New Ionic Liquids Incorporating Chiral Cations and/or Chiral Anions

  摘要：

  The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants. Chiral ionic liquids containing anions such as Cl-, Br-, TsO-, PF6-, NO3-, CF3SO3-, and (+)- and (-)-C6H5CH(OH)C(O)O- were synthesized using (-)-(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl [(-)-(1R)-nopyl] halides (X = Cl, Br) and tosylate in 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent on the applied concentration. The lowest concentration causing a distinct reduction in plant germination/growth was 100 mg/kg. Spring barley better tolerated the ionic liquids (200 mg/kg) than common radish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability of seeds. The starting N-methylimidazole used in lower concentrations (1 and 10 mg/kg of soil dry weight) was not phytotoxic, in contrast to higher doses (> 1000 mg/kg).

  DOI：

  10.1021/jf062849q
• 作为产物：
  描述：

  (1R)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 在 四氯化碳 、 三苯基膦 作用下， 反应 73.0h， 生成 (-)-1-[(1R)-nopyl]-3-methylimidazolium chloride
  参考文献：
  名称：

  Synthesis and Phytotoxicity of New Ionic Liquids Incorporating Chiral Cations and/or Chiral Anions

  摘要：

  The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants. Chiral ionic liquids containing anions such as Cl-, Br-, TsO-, PF6-, NO3-, CF3SO3-, and (+)- and (-)-C6H5CH(OH)C(O)O- were synthesized using (-)-(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl [(-)-(1R)-nopyl] halides (X = Cl, Br) and tosylate in 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent on the applied concentration. The lowest concentration causing a distinct reduction in plant germination/growth was 100 mg/kg. Spring barley better tolerated the ionic liquids (200 mg/kg) than common radish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability of seeds. The starting N-methylimidazole used in lower concentrations (1 and 10 mg/kg of soil dry weight) was not phytotoxic, in contrast to higher doses (> 1000 mg/kg).

  DOI：

  10.1021/jf062849q

文献信息

• Synthesis and Phytotoxicity of New Ionic Liquids Incorporating Chiral Cations and/or Chiral Anions
  作者：Piotr Bałczewski、Barbara Bachowska、Tomasz Białas、Robert Biczak、Wanda M. Wieczorek、Agnieszka Balińska

  DOI：10.1021/jf062849q

  日期：2007.3.1

  The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants. Chiral ionic liquids containing anions such as Cl-, Br-, TsO-, PF6-, NO3-, CF3SO3-, and (+)- and (-)-C6H5CH(OH)C(O)O- were synthesized using (-)-(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl [(-)-(1R)-nopyl] halides (X = Cl, Br) and tosylate in 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent on the applied concentration. The lowest concentration causing a distinct reduction in plant germination/growth was 100 mg/kg. Spring barley better tolerated the ionic liquids (200 mg/kg) than common radish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability of seeds. The starting N-methylimidazole used in lower concentrations (1 and 10 mg/kg of soil dry weight) was not phytotoxic, in contrast to higher doses (> 1000 mg/kg).