(benzotriazol-1-yl)(2-hydroxyphenyl)methanone | 347370-91-6

• 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: (benzotriazol-1-yl)(2-hydroxyphenyl)methanone
• 英文别名: (1H-benzo[d][1,2,3]triazol-1-yl)(2-hydroxyphenyl)methanone；2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)phenol；2-(1H-1,2,3-Benzotriazole-1-carbonyl)phenol；benzotriazol-1-yl-(2-hydroxyphenyl)methanone
• CAS: 347370-91-6
• 化学式: C₁₃H₉N₃O₂
• 分子量: 239.233
• InChiKey: MYHCFYDWOKNXIO-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  461.0±47.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (benzotriazol-1-yl)(2-hydroxyphenyl)methanone 在 sodium azide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以97%的产率得到2-苯并唑啉酮
  参考文献：
  名称：

  由N-酰基苯并三唑有效地一锅合成N，N [伯或分钟]-二取代的尿素和氨基甲酸酯

  摘要：

  已经设计了由N-酰基苯并三唑容易且高产率的一锅合成氨基甲酸酯和N，N′-二取代的对称脲。据信，中间的酰基叠氮化物经历了Curtius重排并且在不同的条件下...

  DOI：

  10.1039/c6ra14131e
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 18.0h， 生成 (benzotriazol-1-yl)(2-hydroxyphenyl)methanone
  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

• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• Direct Synthesis of Esters and Amides from Unprotected Hydroxyaromatic and -aliphatic Carboxylic Acids
  作者：Alan R. Katritzky、Sanjay K. Singh、Chunming Cai、Sergey Bobrov

  DOI：10.1021/jo052293q

  日期：2006.4.1

  activation of hydroxy-substituted carboxylic acids using benzotriazole chemistry without prior protection of the hydroxy substituents is presented. The N-acylbenzotriazole intermediates 2a−g, 6a−d, and 9a−c have been used for high-yielding synthesis of both aliphatic (3a−l) and aromatic (7a−h, 10a−f) hydroxy carboxamides. High yields of aromatic hydroxy esters 12a−h and 13a−i were obtained using either

  提出了一种在不事先保护羟基取代基的情况下使用苯并三唑化学方法活化羟基取代的羧酸的简便方法。所述Ñ -acylbenzotriazole中间体2A -克，6A - d，和图9a - ç已被用于脂族的高产合成（图3a -升）和芳族（图7a - ħ，10A - ˚F羟基羧酰胺）。芳族羟基酯12a - h和13a - i的高收率使用在中性微波条件下的纯醇或亲核醇盐和中间体N-（芳基）苯并三唑可制得苯二酚。在脂族羟基酯11a，b和硫醇酸酯11e - g的情况下，从中间体2a - c获得中等产率。
• Pharmacokinetic and <i>In Vivo</i> Efficacy Studies of the Mycobactin Biosynthesis Inhibitor Salicyl-AMS in Mice
  作者：Shichun Lun、Haidan Guo、John Adamson、Justin S. Cisar、Tony D. Davis、Sivagami Sundaram Chavadi、J. David Warren、Luis E. N. Quadri、Derek S. Tan、William R. Bishai

  DOI：10.1128/aac.00918-13

  日期：2013.10

  Mycobactin biosynthesis in Mycobacterium tuberculosis facilitates iron acquisition, which is required for growth and virulence. The mycobactin biosynthesis inhibitor salicyl-AMS [5′- O -( N -salicylsulfamoyl)adenosine] inhibits M. tuberculosis growth in vitro under iron-limited conditions. Here, we conducted a single-dose pharmacokinetic study and a monotherapy study of salicyl-AMS with mice. Intraperitoneal injection yielded much better pharmacokinetic parameter values than oral administration did. Monotherapy of salicyl-AMS at 5.6 or 16.7 mg/kg significantly inhibited M. tuberculosis growth in the mouse lung, providing the first in vivo proof of concept for this novel antibacterial strategy.

  摘要 结核分枝杆菌中分枝杆菌素的生物合成 结核分枝杆菌 促进铁的获得，而铁是生长和毒力所必需的。分枝菌素生物合成抑制剂水杨酰-AMS [5′- O -( N 水杨酰-AMS[5′- O -（N 结核杆菌 生长 体外 在铁限制条件下抑制结核杆菌的体外生长。在此，我们对小鼠进行了水杨酰-AMS 的单剂量药代动力学研究和单药治疗研究。腹腔注射获得的药代动力学参数值远高于口服给药。5.6 或 16.7 毫克/千克剂量的水杨酰-AMS 单药疗法可显著抑制 结核杆菌 在小鼠肺部的生长，首次在 体内 证明了这种新型抗菌策略的概念。
• Concise Modular Synthesis and NMR Structural Determination of Gallium Mycobactin T
  作者：Kiat Hwa Chan、John T. Groves

  DOI：10.1021/acs.joc.1c01966

  日期：2021.11.5

  A modular synthesis of mycobactin T and its N-acetyl analogue is reported in a route that facilitates permutation of the lipid tails. A key feature is the generation of N(α)-Cbz-N(ε)-benzyloxy-N(ε)-Boc-lysine (A4) with methyl(trifluoromethyl)dioxirane in 59% yield. Selective hydroxamate N-acylation was achieved with acyl fluorides, enabling installation of lipids tails in the final step. O-Benzyl-dehydrocobactin

  在促进脂质尾部排列的途径中报道了分枝杆菌素 T 及其N-乙酰类似物的模块化合成。一个关键特征是 N(α)-Cbz-N(ε)-苄氧基-N(ε)-Boc-赖氨酸 ( A4 ) 与甲基（三氟甲基）二环氧乙烷的生成率为 59%。使用酰氟实现选择性异羟肟酸N-酰化，从而能够在最后一步中安装脂质尾部。O -Benzyl-dehydrocobactin T ( B4 ) 通过修改已知的五步序列制备，总产率为 49%。2-羟基苯基-4-羧基恶唑啉 ( C3 ) 由 2-羟基苯甲酸和l-丝氨酸甲酯分三步，总收率为55%。A4和B4与 EDCI的酯偶联以 73% 的产率提供MbI-1。用 Pd/BaSO 4和 50 psi 的 H 2催化氢化同时进行烯烃还原和脱苄基化，以 96% 的收率得到MbI-2。片段C3被转化为酰氟C4，其与MbI-2偶联以 51% 的产率得到MbI-3。最后，用 HCl/EtOAc 去除
• Synthesis of Benzoxazines, Quinazolines and 4H-Benzo[e][1,3]thiazine by ANRORC Rearrangements of 1,2,4-Oxadiazoles
  作者：Alan Katritzky、Bogdan Draghici、Bahaa El-Gendy

  DOI：10.1055/s-0031-1289673

  日期：2012.2

  1,2,4-Oxadiazoles undergo ANRORC (addition of nucleophile, ring-opening and ring-closure) rearrangements upon reaction with excess of n-butyllithium to give benzoxazines, benzothiazines, and quinazolines in good yields under mild conditions. N,O-heterocycles - rearrangements - benzoxazines - quinazolines - benzothiazines

  1,2,4-恶二唑经历ANRORC（一个的ddition Ñ ucleophile，- [R ing- ö pening和- [R ing- Ç losure）重排在与过量的反应Ñ丁基锂，得到苯并恶嗪，苯并噻嗪，并且在在温和良好的收率的喹唑啉条件。 N，O杂环-重排-苯并恶嗪-喹唑啉-苯并噻嗪