1-(biphenyl-4-ylmethyl)-1H-benzotriazole | 203069-98-1

• 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-(biphenyl-4-ylmethyl)-1H-benzotriazole
• 英文别名: N-(4-phenylbenzyl)-1H-benzotriazole；1-[(4-Phenylphenyl)methyl]benzotriazole
• CAS: 203069-98-1
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: FAFBDZAJPWABST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(biphenyl-4-ylmethyl)-1H-benzotriazole 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 3-Chloro-benzoic acid benzotriazol-1-yl-biphenyl-4-yl-methyl ester
  参考文献：
  名称：

  [（芳基）（phenylseleno）甲基] - - ，1 - [（芳基）（芳硫基） - （phenylseleno）甲基] - ，和1 - [（芳基）（diphenylseleno）甲基]苯并三唑与1氧化米氯过苯甲酸

  摘要：

  在过去的十年中，苯并三唑（1）作为一种出色的合成助剂受到了广泛的关注[1]。最近，Katritzky等人。[ 2 ]研究了1-（phenylthiomethyl）benzotriazole（2a）和1-（2-phenyl-1-phenylthioethyl）benzotriazole（2b）的氧化，并通过wj-氯过苯甲酸（m -CPBA）处理获得了它们的砜和亚砜。和高碘酸钠。没有分离出衍生自前述化合物的α-碳和N-1原子之间的杂位裂解的化合物。

  DOI：

  10.1002/jhet.5570340617
• 作为产物：
  描述：

  T406石油添加剂 在 四(三苯基膦)钯 、 sodium hexamethyldisilazane 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 4.67h， 生成 1-(biphenyl-4-ylmethyl)-1H-benzotriazole
  参考文献：
  名称：

  Fragment Based Optimization of Metabotropic Glutamate Receptor 2 (mGluR2) Positive Allosteric Modulators in the Absence of Structural Information

  摘要：

  Metabotropic glutamate receptor 2 (mGluR2) positive allosteric modulators (PAMs) have been implicated as potential pharmacotherapy for psychiatric conditions. Screening our corporate compound deck, we identified a benzotriazole fragment (4) that was rapidly optimized to a potent and metabolically stable early lead (16). The highly lipophilic character of 16, together with its limited solubility, permeability, and high protein binding, however, did not allow reaching of the proof of concept in vivo. Since further attempts on the optimization of druglike properties were unsuccessful, the original hit 4 has been revisited and was optimized following the principles of fragment based drug discovery (FBDD). Lacking structural information on the receptor ligand complex, we implemented a group efficiency (GE) based strategy and identified a new fragment like lead (60) with more balanced profile. Significant improvement achieved on the druglike properties nominated the compound for in vivo proof of concept studies that revealed the chemotype being a promising PAM lead targeting mGluR2 receptors.

  DOI：

  10.1021/acs.jmedchem.8b00161

文献信息

• Highly effective alternative aryl trihydroxyborate salts for a ligand-free, on-water Suzuki–Miyaura coupling reaction
  作者：Basudeb Basu、Kinkar Biswas、Sekhar Kundu、Sujit Ghosh

  DOI：10.1039/c0gc00122h

  日期：——

  Aryl trihydroxyborate salts of sodium, an easily accessible and stable alternative source of organoboron species, can efficiently promote Pd-catalyzed ligand-free, on-water Suzuki–Miyaura (SM) coupling reactions at ambient temperature.

  钠的芳基三羟基硼酸盐是一种易于获取且稳定的有机硼化合物替代源，能够在常温下有效促进钯催化的无配体水相铃木-宫浦（SM）偶联反应。
• Synthesis of 1<i>H</i>-Benzotriazoles via Reductive Amination on Solid Supports
  作者：Stefan Bräse、Viktor Zimmermann、Rainhard Müller

  DOI：10.1055/s-2008-1032014

  日期：2008.1

  An efficient synthesis of N-benzyl-1H-benzotriazoles utilizing a two-step reductive amination reaction on solid supports has been achieved. The method is suitable for combinatorial synthesis.

  利用固体支持物上的两步还原胺化反应，实现了 N-苄基-1H-苯并三唑的高效合成。该方法适用于组合合成。
• Fragment Based Optimization of Metabotropic Glutamate Receptor 2 (mGluR2) Positive Allosteric Modulators in the Absence of Structural Information
  作者：György Szabó、György I. Túrós、Sándor Kolok、Mónika Vastag、Zsuzsanna Sánta、Miklós Dékány、György I. Lévay、István Greiner、Minami Natsumi、Watanabe Tatsuya、György M. Keserű

  DOI：10.1021/acs.jmedchem.8b00161

  日期：2019.1.10

  Metabotropic glutamate receptor 2 (mGluR2) positive allosteric modulators (PAMs) have been implicated as potential pharmacotherapy for psychiatric conditions. Screening our corporate compound deck, we identified a benzotriazole fragment (4) that was rapidly optimized to a potent and metabolically stable early lead (16). The highly lipophilic character of 16, together with its limited solubility, permeability, and high protein binding, however, did not allow reaching of the proof of concept in vivo. Since further attempts on the optimization of druglike properties were unsuccessful, the original hit 4 has been revisited and was optimized following the principles of fragment based drug discovery (FBDD). Lacking structural information on the receptor ligand complex, we implemented a group efficiency (GE) based strategy and identified a new fragment like lead (60) with more balanced profile. Significant improvement achieved on the druglike properties nominated the compound for in vivo proof of concept studies that revealed the chemotype being a promising PAM lead targeting mGluR2 receptors.
• Oxidation of 1-[(aryl)(phenylseleno)methyl]-, 1-[(aryl)(arylthio)-(phenylseleno)methyl]-, and l-[(aryl)(diphenylseleno)methyl]benzotriazoles with<i>m</i>-chloroperbenzoic acid
  作者：Yoon Ho Kang、Kyongtae Kim

  DOI：10.1002/jhet.5570340617

  日期：1997.11

  During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1-(phenylthiomethyl)benzotriazole (2a) and 1-(2-phenyl-1-phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with wj-chloroperbenzoic acid (m-CPBA) and sodium periodate, respectively. No compounds

  在过去的十年中，苯并三唑（1）作为一种出色的合成助剂受到了广泛的关注[1]。最近，Katritzky等人。[ 2 ]研究了1-（phenylthiomethyl）benzotriazole（2a）和1-（2-phenyl-1-phenylthioethyl）benzotriazole（2b）的氧化，并通过wj-氯过苯甲酸（m -CPBA）处理获得了它们的砜和亚砜。和高碘酸钠。没有分离出衍生自前述化合物的α-碳和N-1原子之间的杂位裂解的化合物。