1-benzyloxy-5-methyl-1,2,3-triazole | 198754-55-1

• 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: 1-benzyloxy-5-methyl-1,2,3-triazole
• 英文别名: 5-Methyl-1-phenylmethoxytriazole
• CAS: 198754-55-1
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: JNYRYVJBZWFQQR-UHFFFAOYSA-N

物化性质

• 沸点：
  326.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-5-methyl-1,2,3-triazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以99%的产率得到5-Methyl-[1,2,3]triazol-1-ol
  参考文献：
  名称：

  Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole

  摘要：

  1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.

  DOI：

  10.1021/jo971313o
• 作为产物：
  描述：

  Glyoxal-mono-O-benzyloxim 在 正丁基锂 、 一水合肼 、 copper(II) sulfate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 10.08h， 生成 1-benzyloxy-5-methyl-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole

  摘要：

  1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.

  DOI：

  10.1021/jo971313o

文献信息

• Novel 1-Hydroxyazole Bioisosteres of Glutamic Acid. Synthesis, Protolytic Properties, and Pharmacology
  作者：Tine B. Stensbøl、Peter Uhlmann、Sandrine Morel、Birgitte L. Eriksen、Jakob Felding、Hasse Kromann、Mette B. Hermit、Jeremy R. Greenwood、Hans Braüner-Osborne、Ulf Madsen、Finn Junager、Povl Krogsgaard-Larsen、Mikael Begtrup、Per Vedsø

  DOI：10.1021/jm010303j

  日期：2002.1.1

  synaptosomal [3H]D-aspartic acid uptake (IC(50) = 93 +/- 25 microM), as well as excitatory amino acid transporters (EAATs) EAAT1 (IC(50) = 100 +/- 30 microM) and EAAT2 (IC(50) = 300 +/- 80 microM). By contrast, compound 8b showed no appreciable affinity for Glu uptake sites, neither synaptosomal nor cloned. Compounds 9a-c and 10a,b, possessing 1-hydroxyimidazole as the terminal acidic function, were devoid

  合成了多种1-羟基唑衍生物，作为（S）-谷氨酸（Glu）的生物等排体和AMPA受体激动剂（R，S）-2-氨基-3-（3-羟基-5-甲基- 4-异恶唑基）丙酸（AMPA，3b）。所有化合物均进行了体外药理研究，包括一系列Glu受体结合测定，天然和克隆Glu摄取系统的摄取研究以及电生理大鼠皮层切片模型。化合物7a，b（带有1-羟基-5-吡唑基部分作为远端羧基官能团的AMPA类似物）仅对[3H] AMPA受体结合位点具有中等亲和力（IC（50）= 2.7 +/- 0.4 microM和IC （50）分别为2.6 +/- 0.6 microM），与大鼠皮质楔形模型的电生理数据相关（EC（50）= 280 +/- 48 microM，EC（50）= 586 +/- 41 microM，分别）。化合物8a，b的AMPA的1-羟基-1,2,3-三唑-5-基类似物对[3H] AMPA受体结合位点表现出高亲和力（IC（50）=