1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester | 106308-55-8

• 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-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate；dimethyl 1-[(2-fluorophenyl)methyl]triazole-4,5-dicarboxylate
• CAS: 106308-55-8
• 化学式: C₁₃H₁₂FN₃O₄
• 分子量: 293.254
• InChiKey: YNQOPEURYRMULB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester 在 盐酸 、 水 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  1,2,3-Triazolo[4,5-d]pyridazines

  摘要：

  Starting from the appropriate azides ( 4-chlorobenzyl-, 2-thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazides) agreeing with the substituent determining four series of derivatives (a-d), some 4-amino-substituted 1,2,3-triazolo[4,5-d]pyridazines (4a-d) corresponding to previously prepared derivatives were obtained by a well experimented synthetic route. Other new derivatives (6c,e) which were different from 4a-d because a chlorine atom had substituted the hydroxyl or the tautomeric oxamido group in the 7 position of the triazolopyridazine ring, were prepared from the suitable azides (2-fluorobenzyl and 2-chlorobenzyl), which similarly determine the series c and e, respectively, via the 4,7-dichloro derivatives 5. The radioligand binding assays at bovine brain adenosine A(1) and A(2A) receptors showed that some compounds 4 possessed high affinity and selectivity for the A(1) receptor subtype whilst binding affinity decreased in compounds 6 indicating the importance of a hydrogen bond donor in the 7 position of the triazolopyridazine ring. It is worth noting that compounds bearing the new lipophilic substituents 2-fluorobenzyl and 2-thiophenemethyl in the 1 position of the triazolopyridazine ring were the most active in the series. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00072-5
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 1-(叠氮甲基)-2-氟苯 以 neat (no solvent) 为溶剂， 以92 %的产率得到1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  高度区域选择性一步合成1-苄基-5-甲酰基-1,2,3-三唑-4-甲酸酯

  摘要：

  开发了一种新的方法，可在温和条件下一步制备 1,4,5-三取代的 1-苄基-5-甲酰基-1,2,3-三唑-4-羧酸酯。该方法包括使用三叔丁氧基氢化铝锂将酯官能团还原为醛。特别是，该方法为完全取代的1,2,3-三唑提供了不同的视角，具有高区域选择性和高产率。使用 FTIR、 1 H、13 C NMR 光谱、HRMS、先进 NMR 技术（COSY、C-APT、HSQC 和 HMBC）和 X 射线晶体学验证了完全取代的三唑的结构。

  DOI：

  10.1007/s10593-023-03192-0

文献信息

• Aralkyltriazole compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04789680A1

  公开（公告）日：1988-12-06

  1-phenyl-lower alkyl-1H-1,2,3-triazole compounds of the formula ##STR1## in which Ph represents phenyl substituted by up to and including 3 substituents selected from lower alkyl, halogen and trifluoromethyl, alk represents lower alkylidene, and wherein either R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkylamino, N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl or R.sub.1 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents hydrogen or lower alkyl, have anti-convulsive properties and can be used as medicaments.

  1-苯基-低级烷基-1H-1,2,3-三唑化合物，其分子式为##STR1##，其中Ph代表苯基，苯基可被低级烷基、卤素和三氟甲基中的一种或多种取代基取代，alk代表低级烷基亚基，且R.sub.1代表氢、低级烷基、低级烷氧基、氨基、N-低级烷基氨基、N,N-二低级烷基氨基、N-低级烷氧酰氨基、碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，而R.sub.2代表碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，或者R.sub.1代表碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，而R.sub.2代表氢或低级烷基，这些化合物具有抗惊厥性质，可用作药物。
• US4789680A
  申请人：——

  公开号：US4789680A

  公开（公告）日：1988-12-06
• CN116874438
  申请人：——

  公开号：——

  公开（公告）日：——
• 1,2,3-Triazolo[4,5-d]pyridazines
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Clementina Manera、Valerio Scartoni、Laura Betti、Gino Giannaccini、Antonio Lucacchini

  DOI：10.1016/s0014-827x(99)00072-5

  日期：1999.9

  Starting from the appropriate azides ( 4-chlorobenzyl-, 2-thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazides) agreeing with the substituent determining four series of derivatives (a-d), some 4-amino-substituted 1,2,3-triazolo[4,5-d]pyridazines (4a-d) corresponding to previously prepared derivatives were obtained by a well experimented synthetic route. Other new derivatives (6c,e) which were different from 4a-d because a chlorine atom had substituted the hydroxyl or the tautomeric oxamido group in the 7 position of the triazolopyridazine ring, were prepared from the suitable azides (2-fluorobenzyl and 2-chlorobenzyl), which similarly determine the series c and e, respectively, via the 4,7-dichloro derivatives 5. The radioligand binding assays at bovine brain adenosine A(1) and A(2A) receptors showed that some compounds 4 possessed high affinity and selectivity for the A(1) receptor subtype whilst binding affinity decreased in compounds 6 indicating the importance of a hydrogen bond donor in the 7 position of the triazolopyridazine ring. It is worth noting that compounds bearing the new lipophilic substituents 2-fluorobenzyl and 2-thiophenemethyl in the 1 position of the triazolopyridazine ring were the most active in the series. (C) 1999 Elsevier Science S.A. All rights reserved.
• Highly regioselective one-step synthesis of 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates
  作者：Guler Yagiz Erdemir、Aliye Altundas

  DOI：10.1007/s10593-023-03192-0

  日期：2023.5

  the ester functional group to an aldehyde using lithium tri-tert-butoxyaluminum hydride. Especially, this method offers a different perspective for fully substituted 1,2,3-triazoles with high regioselectivity and high yields. The structure of fully substituted triazoles was verified using FTIR, 1H, 13C NMR spectroscopy, HRMS, advanced NMR techniques (COSY, C-APT, HSQC, and HMBC), and X-ray crystallography

  开发了一种新的方法，可在温和条件下一步制备 1,4,5-三取代的 1-苄基-5-甲酰基-1,2,3-三唑-4-羧酸酯。该方法包括使用三叔丁氧基氢化铝锂将酯官能团还原为醛。特别是，该方法为完全取代的1,2,3-三唑提供了不同的视角，具有高区域选择性和高产率。使用 FTIR、 1 H、13 C NMR 光谱、HRMS、先进 NMR 技术（COSY、C-APT、HSQC 和 HMBC）和 X 射线晶体学验证了完全取代的三唑的结构。