(1S)Methylbenzyl (4R)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate | 173658-96-3

• 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: (1S)Methylbenzyl (4R)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate
• 英文别名: [(1S)-1-phenylethyl] (4R)-5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-4-methyl-3H-pyrazole-4-carboxylate
• CAS: 173658-96-3
• 化学式: C₂₆H₂₃Cl₂N₃O₃
• 分子量: 496.393
• InChiKey: TVRASQLBSFJPGA-MRDQGFSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1S)Methylbenzyl (4R)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate 在 sodium methylate 作用下， 反应 4.0h， 以90%的产率得到Methyl (4R)-3-(4-chlorophenyl)-4-methyl-1-[N-(4-chlorophenyl)carbamoyl]-2-pyrazoline-4-carboxylate
  参考文献：
  名称：

  Stereochemical basis for the insecticidal activity of carbamoylated and acylated pyrazolines

  摘要：

  Methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl] -4-methyl-2-pyrazoline-4-carboxylate was converted to corresponding (1R)- and (1S)-phenethyl esters via its carboxylic acid and acid chloride at the C-4 atom to separate the diastereomers. Their configurations were confirmed by X-ray analysis. Both isomers of the (1R)methylbenzyl ester were subjected to transesterification with sodium methoxide to obtain enantiomers of the starting methyl ester. Their insecticidal activity was measured against American cockroaches (Periplaneta americana (L.)) by injection and against house flies (Musca domestica L.) by topical application under various synergistic conditions with metabolic inhibitors. The activity values of the four alpha-methylbenzyl esters and the R-isomer of the starting methyl ester were similar. The S-enantiomer of the methyl ester was about 10 and 100 times more active than the R-isomer against the cockroach and the fly, respectively. Some N-arylacetyl and N-aryloxyacetyl derivatives of the starting N-(4-chlorophenyl)carbamoyl compound gave very low activity. Conformation-energy profiles for some compounds suggested that the conformation of substituents on the N-1 atom in the pyrazoline ring has a specific role for the potential insecticidal effects.

  DOI：

  10.1002/(sici)1096-9063(199602)46:2<105::aid-ps320>3.0.co;2-y
• 作为产物：
  描述：

  methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (1S)Methylbenzyl (4R)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate
  参考文献：
  名称：

  Stereochemical basis for the insecticidal activity of carbamoylated and acylated pyrazolines

  摘要：

  Methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl] -4-methyl-2-pyrazoline-4-carboxylate was converted to corresponding (1R)- and (1S)-phenethyl esters via its carboxylic acid and acid chloride at the C-4 atom to separate the diastereomers. Their configurations were confirmed by X-ray analysis. Both isomers of the (1R)methylbenzyl ester were subjected to transesterification with sodium methoxide to obtain enantiomers of the starting methyl ester. Their insecticidal activity was measured against American cockroaches (Periplaneta americana (L.)) by injection and against house flies (Musca domestica L.) by topical application under various synergistic conditions with metabolic inhibitors. The activity values of the four alpha-methylbenzyl esters and the R-isomer of the starting methyl ester were similar. The S-enantiomer of the methyl ester was about 10 and 100 times more active than the R-isomer against the cockroach and the fly, respectively. Some N-arylacetyl and N-aryloxyacetyl derivatives of the starting N-(4-chlorophenyl)carbamoyl compound gave very low activity. Conformation-energy profiles for some compounds suggested that the conformation of substituents on the N-1 atom in the pyrazoline ring has a specific role for the potential insecticidal effects.

  DOI：

  10.1002/(sici)1096-9063(199602)46:2<105::aid-ps320>3.0.co;2-y