methyl 5-(2-amino-5-chloro-3-methylphenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate | 1609006-73-6

• 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: methyl 5-(2-amino-5-chloro-3-methylphenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate
• CAS: 1609006-73-6
• 化学式: C₁₃H₁₆ClN₃O₃
• 分子量: 297.741
• InChiKey: WPZJSJFJZLIIMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride 、 methyl 5-(2-amino-5-chloro-3-methylphenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到methyl 5-(5-chloro-2-(1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamido)-3-methylphenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate
  参考文献：
  名称：

  Synthesis and biological activities of 2,3-dihydro-1,3,4-oxadiazole compounds and its derivatives as potential activator of ryanodine receptors

  摘要：

  A series of novel 2,3-dihydro-1,3,4-oxadiazoles containing N-pyridylpyrazole carboxamides moieties were obtained by applying a new synthetic route. Their insecticidal tests against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to excellent activities at the testing concentrations. In particular, compound 6a showed 40% larvicidal activities against oriental armyworm at 1 mg/L, while 7a against diamondback was 100% at 0.01 mg/L. Calcium imaging results demonstrated that 6a, 6d and 7a stimulated a transient elevation in [Ca2+](i) in the absence of external calcium after the central neurons dye loading with fluo-3 AM, implying that these novel compounds were potential activators of the ligand-gated calcium channel on the endoplasmic reticulum. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.077
• 作为产物：
  描述：

  2-氨基-5-氯-3-甲基苯甲酸 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.08h， 生成 methyl 5-(2-amino-5-chloro-3-methylphenyl)-2,2-dimethyl-1,3,4-oxadiazole-3(2H)-carboxylate
  参考文献：
  名称：

  Synthesis and biological activities of 2,3-dihydro-1,3,4-oxadiazole compounds and its derivatives as potential activator of ryanodine receptors

  摘要：

  A series of novel 2,3-dihydro-1,3,4-oxadiazoles containing N-pyridylpyrazole carboxamides moieties were obtained by applying a new synthetic route. Their insecticidal tests against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to excellent activities at the testing concentrations. In particular, compound 6a showed 40% larvicidal activities against oriental armyworm at 1 mg/L, while 7a against diamondback was 100% at 0.01 mg/L. Calcium imaging results demonstrated that 6a, 6d and 7a stimulated a transient elevation in [Ca2+](i) in the absence of external calcium after the central neurons dye loading with fluo-3 AM, implying that these novel compounds were potential activators of the ligand-gated calcium channel on the endoplasmic reticulum. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.077