4-(diethoxymethyl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole | 1354569-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(diethoxymethyl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole
• 英文别名: 2-[4-(Diethoxymethyl)triazol-1-yl]ethanol
• CAS: 1354569-86-0
• 化学式: C₉H₁₇N₃O₃
• 分子量: 215.252
• InChiKey: MEBNVBRAPCPCJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(diethoxymethyl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium tert-butylate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (E)-4-(4-aminostyryl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled Styryltriazole and Resveratrol Derivatives for β-Amyloid Plaque Imaging

  摘要：

  In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for beta-amyloid (A beta) plaque imaging. On the basis of their binding affinities to A beta(1-42) aggregates, the styryltriazole (1, K-i = 12.8 nM) and one resveratrol derivative (5, K-i = 0.49 nM) were labeled with F-18. In normal mice, tissue distribution of [F-18]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [F-18]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [F-18]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [F-18]1 is a desirable PET radioligand for A beta plaque imaging.

  DOI：

  10.1021/jm201400q
• 作为产物：
  描述：

  丙醛二乙基乙缩醛 、 2-叠氮基乙醇 在 copper(II) loaded mesoporous SBA-15 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到4-(diethoxymethyl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Copper(II) SBA-15: A reusable catalyst for azide–alkyne cycloaddition

  摘要：

  The azide-alkyne cycloaddition reaction was investigated under catalytic conditions involving a copper(II) loaded silica based mesoporous material. Cu(II) SBA-15 demonstrated a high catalytic effect in 1,4-triazoles synthesis in organic. No additives such as a base or a reductant are required. Quantitative yields were obtained and a mere filtration of the mesoporous material which retains copper(II) allows the recovery of the catalyst. In addition, up to 5 times recycling of the catalyst was achieved without loss of the activity affording 1,4-triazoles in a yield up to 98%. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.06.003