2-(1H-Benzotriazol-1-ylmethyl)phenol | 132980-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(1H-Benzotriazol-1-ylmethyl)phenol
• 英文别名: o-(Benzotriazol-1-ylmethyl)phenol；2-(1H-1,2,3-Benzotriazol-1-ylmethyl)phenol；2-(benzotriazol-1-ylmethyl)phenol
• CAS: 132980-32-6
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: CFXOATFGYAMSIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  14.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-Benzotriazol-1-ylmethyl)phenol 在 正丁基锂 作用下， 反应 8.0h， 生成 1-[1-(2-Trimethylsilanyloxy-phenyl)-ethyl]-1H-benzotriazole
  参考文献：
  名称：

  Katritzky, Alan R.; Lan, Xiangfu; Zhang, Zhongxing, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 2, p. 381 - 387

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-nitrobenzyl)-1H-benzo[d][1,2,3]triazole 在 palladium on activated charcoal 硫酸 、 氢气 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 生成 2-(1H-Benzotriazol-1-ylmethyl)phenol
  参考文献：
  名称：

  New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators. IV

  摘要：

  This paper reports the synthesis of a series of new 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, which have been tested for their activity as possible activators of potassium channels. In rat aortic rings, the 'opened' derivatives 1a-f, intermediates of synthesis, showed vasorelaxing properties, with appreciable values of potency. However, the most remarkable effects were recorded for the 2-hydroxybenzoylbenzotriazoles 3a-f, which showed full vasorelaxing efficacy and high potency values. The introduction of a 2-hydroxybenzyl substituent in the 1 position of the benzotriazole ring (compound 7) strongly decreased the activity, showing the importance of the electron-acceptor carbonyl function. The best compound, 3b, was further investigated, in order to evaluate the possible mechanism of action involved in the vasodilator activity. In the vascular model, different potassium channel blockers inhibited the effects of the compound, and an increase of the levels of membrane depolarisation induced a significant reduction of the recorded responses. Compound 3b was also tested in a model of isolated rat heart, retroperfused through the aorta and submitted to a global ischemia/reperfusion cycle. In such an experimental condition, 3b showed an interesting cardioprotective activity. All the above observations are in agreement with the hypothesis of a mechanism linked to the activation of potassium channels. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01146-6

文献信息

• Design, step-economical diversity-oriented synthesis of an N-heterocyclic library containing a pyrimidine moiety: discovery of novel potential herbicidal agents
  作者：Dong Ma、Yang Yin、Ying-Lu Chen、Yi-Tao Yan、Jun Wu

  DOI：10.1039/d1ra02663a

  日期：——

  The synthesis of highly diverse libraries has become of paramount importance for obtaining novel leads for drug and agrochemical discovery. Herein, the step-economical diversity-oriented synthesis of a library of various pyrimidine-N-heterocycle hybrids was developed, in which a 4,6-dimethoxypyrimidine core was incorporated into nine kinds of N-heterocycles. A total of 34 structurally diverse compounds

  高度多样化的文库的合成对于获得药物和农用化学品发现的新先导化合物变得至关重要。在此，开发了各种嘧啶-N-杂环杂化物文库的步骤经济的多样性导向合成方法，其中将4,6-二甲氧基嘧啶核心掺入九种N-杂环中。总共 34 种结构不同的化合物是通过两步法从非常简单且市售的起始材料合成的。此外，该文库的体内生物筛选鉴定出 11 种活性化合物，这些化合物在每公顷 750 g ai 剂量下对 D. sanguinalis 表现出良好的芽后除草活性。更重要的是，嘧啶-四氢咔唑杂化物5q在相同剂量下对五种测试杂草表现出良好至优异的除草活性。嘧啶-四氢咔唑杂化物代表了一类新型除草剂，可能成为除草剂发现过程中有前途的先导化合物。
• o-(.alpha.-Benzotriazolylalkyl)phenols: Novel Precursors for the Preparation of 1,1-Bis(2-hydroxyaryl)alkanes
  作者：Alan R. Katritzky、Zhongxing Zhang、Hengyuan Lang、Xiangfu Lan

  DOI：10.1021/jo00103a009

  日期：1994.12

  Reactions of o-(alpha-benzotriazolylalkyl)phenols with a variety of substituted phenols and naphthols in the presence of a base provide efficient access to symmetrical and more importantly to unsymmetrical 1,1-bis(2-hydroxyaryl)alkanes.
• O-(.alpha.-Benzotriazolylalkyl)phenols: Novel Precursors for the Preparation of Ortho-Substituted Phenols via Intermediate 0-Quinone Methides
  作者：Alan R. Katritzky、Zhongxing Zhang、Xiangfu Lan、Hengyaun Lang

  DOI：10.1021/jo00086a050

  日期：1994.4
• Convenient Synthesis of 1<i>H</i>-Benzotriazolylalkylphenols
  作者：Vitalij A. Osyanin、Natalia E. Sidorina、Yuri N. Klimochkin

  DOI：10.1080/00397911.2011.563452

  日期：2012.9.15

  A simple, efficient, and environmentally benign method has been developed for the exclusive formation of synthetically significant 1H-benzotriazol-1-ylalkylphenols from hydroxybenzyl alcohols and benzotriazole.
• Katritzky, Alan R.; Lan, Xiangfu; Lam, Jamshed N., Chemische Berichte, 1991, vol. 124, # 8, p. 1809 - 1817
  作者：Katritzky, Alan R.、Lan, Xiangfu、Lam, Jamshed N.

  DOI：——

  日期：——

表征谱图