3-(4-hydroxyphenyl)-2-(1H-tetrazol-1-yl)propanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-hydroxyphenyl)-2-(1H-tetrazol-1-yl)propanoic acid
• 英文别名: (S)-3-(4-hydroxyphenyl)-2-(1H-tetrazol-1-yl)propanoic acid；(2S)-3-(4-hydroxyphenyl)-2-(tetrazol-1-yl)propanoic acid
• 化学式: C₁₀H₁₀N₄O₃
• mdl: MFCD15730781
• 分子量: 234.214
• InChiKey: SCCRFEBXGLILKF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-酪氨酸 、 原甲酸三乙酯 在 sodium azide 作用下， 以 乙醇 为溶剂， 以64%的产率得到3-(4-hydroxyphenyl)-2-(1H-tetrazol-1-yl)propanoic acid
  参考文献：
  名称：

  Copper nanoparticles: A capable and versatile catalyst for the synthesis of diverse 1-phenyl-1H-tetrazoles from amino acids

  摘要：

  Cu nanoparticles were prepared in successive stages: preparation of the Fe3O4 magnetic nanoparticles (Fe3O4 MNPs), coating of the Fe3O4 MNPs with tetraethyl orthosilicate (Fe3O4@SiO2), functionalization of Fe3O4@SiO2 with 3-chloropropyltrimethoxysilane (CPTMS) and 4-amino-1,2,4-triazole (AT) ligands (Fe3O4@SiO2@CPTMS@AT), and the complexation of Fe3O4@SiO2@CPTMS@AT with CuCl2 (Fe3O4@SiO2@CPTMS@AT@Cu). The obtained Cu nano-catalyst was then used for the synthesis of diverse tetrazoles from the reaction of various amino acids with sodium azide and triethyl orthoformate (TEOF) in ethanol at 80 degrees C. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.12.037

文献信息

• Enantioselectivity of the reaction of α-amino acids with sodium azide and triethyl orthoformate in the synthesis of tetrazoles
  作者：S. S. Chuprun、A. V. Protas、O. S. Fedorova、D. D. Vaulina、R. N. Krasikova、E. A. Popova、R. E. Trifonov

  DOI：10.1134/s1070428016120307

  日期：2016.12

  enantioselectivity of such reactions remains unresolved. In this work we used enantiomerically pure Land D-amino acids and their benzyl esters 1a–1g to synthesize the corresponding 2-(1H-tetrazol-1-yl)acetic acids 2a–2g. The substrates were amino acids of different natures, including aliphatic and aromatic amino acids, amino dicarboxylic acid benzyl esters, and those containing an ester group in the side chain

  四唑基衍生物或氨基酸类似物是新药设计中重要的药效团片段 [1, 2]。1-取代的 1H-四唑可以通过伯胺与叠氮化钠和原酸酯的杂环化合成 [1, 3-6]。我们之前报道了在离不对称碳原子相当远的侧链中含有 1H-四唑-1-基片段的天然氨基酸类似物的合成，从而保留了它们的光学纯度 [7, 8]。此类化合物用于例如肽模拟物的合成[8]。Voitekhovich 等人。[9] 描述了通过 α-氨基酸与叠氮化钠和原甲酸三乙酯反应合成四唑-1-基乙酸衍生物的方法。然而，没有讨论产品的光学纯度。考虑到α-氨基酸中的氨基直接与不对称碳原子相连，这种反应的对映选择性问题仍未解决。在这项工作中，我们使用对映体纯的 Land D-氨基酸及其苄酯 1a-1g 合成相应的 2-(1H-四唑-1-基)乙酸 2a-2g。底物是不同性质的氨基酸，包括脂肪族和芳香族氨基酸、氨基二羧酸苄酯以及在侧链中含有酯基的氨基酸。通过在
• Copper nanoparticles: A capable and versatile catalyst for the synthesis of diverse 1-phenyl-1H-tetrazoles from amino acids
  作者：Maryam Ariannezhad、Davood Habibi、Somayyeh Heydari

  DOI：10.1016/j.poly.2018.12.037

  日期：2019.3

  Cu nanoparticles were prepared in successive stages: preparation of the Fe3O4 magnetic nanoparticles (Fe3O4 MNPs), coating of the Fe3O4 MNPs with tetraethyl orthosilicate (Fe3O4@SiO2), functionalization of Fe3O4@SiO2 with 3-chloropropyltrimethoxysilane (CPTMS) and 4-amino-1,2,4-triazole (AT) ligands (Fe3O4@SiO2@CPTMS@AT), and the complexation of Fe3O4@SiO2@CPTMS@AT with CuCl2 (Fe3O4@SiO2@CPTMS@AT@Cu). The obtained Cu nano-catalyst was then used for the synthesis of diverse tetrazoles from the reaction of various amino acids with sodium azide and triethyl orthoformate (TEOF) in ethanol at 80 degrees C. (C) 2018 Elsevier Ltd. All rights reserved.