4-((1-(2,4,4-trimethylpentan-2-yl)-1H-tetrazol-5-yl)methyl)morpholine | 1340483-97-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((1-(2,4,4-trimethylpentan-2-yl)-1H-tetrazol-5-yl)methyl)morpholine
• 英文别名: 4-[(1-(1,1,3,3-tetramethylbutyl)-1H-tetrazol-5-yl)methyl]morpholine；4-[[1-(2,4,4-Trimethylpentan-2-yl)tetrazol-5-yl]methyl]morpholine
• CAS: 1340483-97-7
• 化学式: C₁₄H₂₇N₅O
• 分子量: 281.401
• InChiKey: SGQPMBRTZXASOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((1-(2,4,4-trimethylpentan-2-yl)-1H-tetrazol-5-yl)methyl)morpholine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 ((1H-tetrazole-5-yl)methyl)morpholine
  参考文献：
  名称：

  1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction

  摘要：

  Easy to perform, functional group tolerant, and short syntheses of the privileged scaffold oxadiazole are highly desired. Here, a metal-free protocol for MCR-based synthesis of 2,5-disubstituted 1,3,4-oxadiazoles via a Ugi-tetrazole/Huisgen sequence was developed. Optimization and scope and limitations of this short and general sequence are described. The reaction was also successfully performed on a gram scale.

  DOI：

  10.1021/acs.orglett.9b02614
• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 1,1,3,3-四甲基丁基异腈 在 叠氮基三甲基硅烷 作用下， 以 甲醇 为溶剂， 反应 12.5h， 以86%的产率得到4-((1-(2,4,4-trimethylpentan-2-yl)-1H-tetrazol-5-yl)methyl)morpholine
  参考文献：
  名称：

  1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction

  摘要：

  Easy to perform, functional group tolerant, and short syntheses of the privileged scaffold oxadiazole are highly desired. Here, a metal-free protocol for MCR-based synthesis of 2,5-disubstituted 1,3,4-oxadiazoles via a Ugi-tetrazole/Huisgen sequence was developed. Optimization and scope and limitations of this short and general sequence are described. The reaction was also successfully performed on a gram scale.

  DOI：

  10.1021/acs.orglett.9b02614

文献信息

• Aminomethyltetrazoles as potential inhibitors of the γ-aminobutyric acid transporters mGAT1–mGAT4: Synthesis and biological evaluation
  作者：Eva S. Schaffert、Georg Höfner、Klaus T. Wanner

  DOI：10.1016/j.bmc.2011.08.039

  日期：2011.11

  1,5-Disubstituted and 5-monosubstituted aminomethyltetrazole derivatives derived from glycine were synthesized employing a TMSN3-modified variant of the Ugi reaction as a key step. All compounds were evaluated regarding their inhibitory potency and subtype selectivity at the four murine GABA transporter subtypes mGAT1–mGAT4. Though none of the 5-monosubstituted tetrazoles turned out to inhibit [3H]GABA

  以Ugi反应的TMSN 3修饰的变体为关键步骤，合成了衍生自甘氨酸的1，5-二取代和5-单取代的氨基甲基四唑衍生物。对所有化合物在四种鼠类GABA转运蛋白亚型mGAT1–mGAT4上的抑制力和亚型选择性进行了评估。尽管没有5取代的四唑类化合物能抑制[ 3H] GABA的吸收程度很高，1，5-二取代的四唑衍生物表现出独特的活性，尤其是在GABA转运蛋白mGAT2-mGAT4处。因此，发现了合理的有效和选择性的mGAT3抑制剂。另外，鉴定出另外两种化合物是mGAT2的有效抑制剂。这是特别相关的，因为到目前为止，只有很少几种不影响mGAT1的有效mGAT2抑制剂是已知的。