1H-苯并三唑-1-乙腈 | 111198-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1H-苯并三唑-1-乙腈
• 中文别名: 1H-苯并噻唑-2-乙腈；苯并三氮唑-1-乙腈；苯并三氮唑1-乙腈
• 英文名称: 1-(cyanomethyl)benzotriazole
• 英文别名: 2-(1H-benzotriazol-1-yl)acetonitrile；2-(benzotriazol-1-yl)acetonitrile；benzotriazol-1-yl-acetonitrile；2-(1H-benzo[d][1,2,3]triazol-1-yl)acetonitrile；1H-benzotriazole-1-acetonitrile
• CAS: 111198-08-4
• 化学式: C₈H₆N₄
• mdl: MFCD00082568
• 分子量: 158.162
• InChiKey: DIFOLZGBHRDEFT-UHFFFAOYSA-N

物化性质

• 熔点：
  84-89 °C (lit.)
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

反应信息

• 作为反应物：
  描述：

  1H-苯并三唑-1-乙腈 在 sodium ethanolate 、 苯甲醛 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到苯并噻唑-1-乙酸
  参考文献：
  名称：

  Synthesis and antitubercular activity of 3-aryl substituted-2-(1H(2H)benzotriazol-1(2)-yl)acrylonitriles#1# Part of this work was presented as a poster communication at the 2nd European Symposium on Antimicrobial Agents, Hradec Kralove, Czech Republic, 1–4 July 1998.

  摘要：

  A series of 22 3-aryl substituted-2-(1H(2H)-benzotriazol-1(2)-yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition & Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, H-1- and C-13-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 mu g/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00144-6
• 作为产物：
  描述：

  1-(氯甲基)-1H-苯并三唑 、 氰化钠 以 二甲基亚砜 为溶剂， 反应 18.0h， 以49%的产率得到1H-苯并三唑-1-乙腈
  参考文献：
  名称：

  Katritzky, Alan R.; Rachwal, Stanislaw; Caster, Kenneth C., Journal of the Chemical Society. Perkin transactions I, 1987, p. 781 - 790

  摘要：

  DOI：

文献信息

• Photochemistry of Benzotriazoles: Generation of 1,3-Diradicals and Intermolecular Cycloaddition as a New Route toward Indoles and Dihydropyrrolo[3,4-b]Indoles
  作者：Nader Al-Jalal、Maher Ibrahim、Nouria Al-Awadi、Mohamed Elnagdi、Yehia Ibrahim

  DOI：10.3390/molecules191220695

  日期：——

  Irradiation of benzotriazoles 1a–e at λ = 254 nm in acetonitrile solution generated the corresponding 1,3-diradicals which underwent intermolecular cycloaddition with maleimides to afford the corresponding dihydropyrrolo[3,4-b]indoles and with acetylene derivatives to afford indoles as the major products. This offers an interesting and simple access to such ring systems of potential synthetic and biological

  在乙腈溶液中以 λ = 254 nm 照射苯并三唑 1a-e 产生相应的 1,3-双自由基，它们与马来酰亚胺进行分子间环加成反应，得到相应的二氢吡咯并 [3,4-b] 吲哚，并用乙炔衍生物得到吲哚作为主要产品。这提供了对具有潜在合成和生物学意义的此类环系统的有趣且简单的访问。光产物的结构是通过光谱和单晶 X 射线晶体学确定的。
• Synthesis and biological evaluation of novel pyrazolo[1,5-a]pyrimidines: Discovery of a selective inhibitor of JAK1 JH2 pseudokinase and VPS34
  作者：Justin D. Singleton、Reuben Dass、Nathaniel R. Neubert、Rachel M. Smith、Zak Webber、Marc D.H. Hansen、Matt A. Peterson

  DOI：10.1016/j.bmcl.2019.126813

  日期：2020.1

  A series of novel 3,6-di-substituted or 3-substituted pyrazolo[1,5-a]pyrimidines were prepared via a microwave-assisted approach that generated a broad array of derivatives in good yields (20-93%, ave. = 59%). The straightforward synthesis involved sequential treatment of commercially-available acetonitrile derivatives with DMF-dimethylacetal (120 °C, 20 min), followed by treatment with NH2NH2·HBr

  通过微波辅助方法制备了一系列新颖的3,6-二取代或3-取代的吡唑并[1,5-a]嘧啶，该方法以良好的收率（20-93％ave）产生了广泛的衍生物。 = 59％）。简单的合成方法包括依次用DMF-二甲基乙缩醛（120°C，20分钟）处理市售的乙腈衍生物，然后用NH2NH2·HBr（120°C，20分钟）和1,1,3,3-处理四甲氧基丙烷或2-芳基取代的丙二醛（120°C，20分钟）。在体外筛选化合物针对MCF7乳腺癌和/或A2780卵巢癌细胞系的抗有丝分裂活性。活性最高的化合物的EC50值为0.5至4.3μM，
• Synthesis and antimicrobial of some new substituted tetrazolomethylbenzo[d]-[1,2,3]triazole derivatives using 1H-benzo[d][1,2,3]triazole as starting material
  作者：Omar M. Ali、Abd El-Galil E. Amr、Elsayed E. Mostafa

  DOI：10.1007/s11164-013-1059-6

  日期：2014.4

  afforded 2-(1H-benzo[d][1,2,3]-triazol-1-yl)acetonitrile 2, which was reacted with sodium azide to give tetrazole derivative 3. Esterification of benzotriazole 1 with ethyl bromoacetate in the presence of anhydrous potassium carbonate afforded ester 4, which was treated with hydrazine hydrate to afford the corresponding hydrazide 5. Reaction of 3 with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide afforded

  一系列tetrazolomethylbenzo [的d ] [1,2,3]三唑衍生物（2 - 14）已被合成并评价为从-1H-苯并[抗微生物剂d ] [1,2,3]三唑（1）作为起始原料。苯并三唑1与氯乙腈的反应得到2-（1H-苯并[ d ] [1,2,3]-三唑-1-基）乙腈2，其与叠氮化钠反应得到四唑衍生物3。在无水碳酸钾存在下用溴乙酸乙酯将苯并三唑1酯化，得到酯4用水合肼处理，得到相应的酰肼5。的反应3与2,3,4,6-四ø -乙酰基α- d吡喃葡萄糖基溴化物，得到nitroglycoside衍生物6，其使用甲醇氨至脱保护的脱乙酰nitroglycoside 7。酰肼5与4,5,6,7-四氯邻苯二甲酸酐或1,2,4,5-苯四甲酸二酐在回流的冰醋酸中反应，分别得到相应的酰亚胺8和9。另外，使酰肼5与二硫化碳在乙醇中反应，得到钾盐。10，与水合肼反应得到氨基三唑衍生物11。使后者化合物与
• 2-aminobenzoxazole derivatives and combinatorial libraries thereof
  申请人：——

  公开号：US20020161028A1

  公开（公告）日：2002-10-31

  The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: 1 wherein R 1 to R 4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.

  本发明涉及以下式子的新型2-氨基苯并噁唑衍生物化合物：其中R1至R4和Z具有本文所提供的含义。本发明还涉及包含两种或更多这类化合物的组合式库，以及制备2-氨基苯并噁唑衍生物化合物的方法。
• Syntheses and transformations of substituted benzazolyl- and tetrazolyl(benzotriazol-1-yl)methanes
  作者：Alan R. Katritzky、Diana Asian、Irina V. Shcherbakova、Jie Chen、Sergei A. Belyakov

  DOI：10.1002/jhet.5570330418

  日期：1996.7

  Condensation reactions of o-hydroxy- and o-mercaptoanilines, and o-phenylenediamine with (benzotriazol-1-yl)acetic acid result in (1,3-benzazol-2-yl)(benzotriazol-1-yl)methanes. Cycloaddition of sodium azide to (benzotriazol-1-yl)acetonitrile leads to (1,2,3,4-tetrazol-5-yl)(benzotriazol-1-yl)methane. The diazolo-substituted benzotriazolylmethanes thus obtained were mono- and di-alkylated at the methylene

  的缩合反应ö羟基和Ò -mercaptoanilines，和ö苯二胺与（苯并三唑-1-基）乙酸在（1,3- benzazol -2-基）（苯并三唑-1-基）甲烷酸的结果。叠氮化钠与（苯并三唑-1-基）乙腈的环加成反应生成（1,2,3,4-四唑-5-基）（苯并三唑-1-基）甲烷。将如此获得的重氮基取代的苯并三唑基甲烷在亚甲基上单和二烷基化，并研究了亲核试剂对苯并三唑基的取代。

表征谱图