1-(叠氮甲基)-3-氯苯 | 126799-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(叠氮甲基)-3-氯苯
• 英文名称: 3-chlorobenzylazide
• 英文别名: 1-(azidomethyl)-3-chlorobenzene；m-chlorobenzyl azide
• CAS: 126799-85-7
• 化学式: C₇H₆ClN₃
• 分子量: 167.598
• InChiKey: WYFWUPTWYUKGQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(叠氮甲基)-3-氯苯 在 potassium phosphate monohydrate 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 4.0h， 以67%的产率得到3-氯苯腈
  参考文献：
  名称：

  A green and efficient access to aryl nitriles via an electrochemical anodic oxidation

  摘要：

  The nitrile functionality is a key building block in synthetic chemistry, and has wide applications in pharmaceuticals. However, traditional methodologies for the synthesis of nitriles are limited to harsh reaction conditions. Herein, we report a new and efficient access to aryl nitriles by an electrochemical synthesis. Compared with the conventional synthetic methods, this electrochemical synthesis is more environmentally friendly and easier to handle. (C) 2014 Zheng-Gen Zha and Zhi-Yong Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.024
• 作为产物：
  描述：

  3-氯苄溴 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以100%的产率得到1-(叠氮甲基)-3-氯苯
  参考文献：
  名称：

  3-取代三唑衍生物的设计合成及生物学评价

  摘要：

  摘要基于吡咯类抗真菌药羊毛甾醇14α-脱甲基酶的活性位点，研究了十六种1-（1H-1,2,4-三唑-1-基）-2-（2,4-二氟苯基）-3-（Nn-已经设计，合成和评估了丁基-N-1-取代的苄基-4-亚甲基-1H-1,2,3-三唑）-2-丙醇作为抗真菌剂。初步针对八种人类病原性真菌的抗真菌试验结果表明，某些化合物具有广谱的优异活性。

  DOI：

  10.1016/j.cclet.2010.11.029

文献信息

• Synthesis of 5-hydroxy- and 5-sulfanyl-substituted [1,2,3]triazolo[4,5-е][1,4]diazepines
  作者：Sergiy V. Kemskiy、Natalia A. Syrota、Andriy V. Bol’but、Viktor I. Dorokhov、Mykhaylo V. Vovk

  DOI：10.1007/s10593-018-2350-7

  日期：2018.8

  5-Amino-N-(2,2-dimethoxyethyl)-1Н-1,2,3-triazole-4-carboxamides in formic acid were subjected to intramolecular cyclization to 5-hydroxy[1,2,3]triazolo[4,5-е][1,4]diazepines, which were converted by treatment with S-nucleophiles to 5-thio-functionalized derivatives.

  5-氨基- ñ - （2,2-二甲氧基乙基）-1- Н 1,2,3-三唑-4-甲酰胺在甲酸进行分子内环化以5-羟基- [1,2,3]三唑并[4 ，5- е ] [1,4]二氮杂,，通过用S-亲核试剂处理将其转化为5-硫代官能化衍生物。
• Structure-Based Optimization of Pyridoxal 5′-Phosphate-Dependent Transaminase Enzyme (BioA) Inhibitors that Target Biotin Biosynthesis in <i>Mycobacterium tuberculosis</i>
  作者：Feng Liu、Surendra Dawadi、Kimberly M. Maize、Ran Dai、Sae Woong Park、Dirk Schnappinger、Barry C. Finzel、Courtney C. Aldrich

  DOI：10.1021/acs.jmedchem.7b00189

  日期：2017.7.13

  relationships (SAR) through the design, synthesis, and biological evaluation of a systematic series of analogues of the original hit using a structure-based drug design strategy, which was enabled by cocrystallization of several analogues with BioA. To confirm target engagement and discern analogues with off-target activity, each compound was evaluated against wild-type (WT) Mtb in biotin-free and -containing

  吡咯醛5'-磷酸（PLP）依赖性转氨酶BioA催化结核分枝杆菌（Mtb）中生物素生物合成的第二步，并且是细菌存活和体内持久性所必需的酶。含有N-芳基，N的有前途的BioA抑制剂6以前已通过基于靶标的全细胞筛选确定了'-苯甲酰基哌嗪支架。在这里，我们使用基于结构的药物设计策略，通过设计，合成和生物学评估原始命中的系统类似物系列，探索结构与活性之间的关系（SAR），该策略是通过将几种类似物与BioA共结晶而实现的。为了确认靶标参与并辨别具有脱靶活性的类似物，评估了每种化合物在无生物素和含培养基的培养基中以及在表达过少和过表达的BioA Mtb菌株中对野生型（WT）Mtb的能力。构象受限的导数36成为最强的K D类似物为76nm针对的bioA和1.7μM（0.6微克/毫升）对的最小抑制浓度的Mtb在无生物素培养基。
• Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- and Dialkylated Amines
  作者：Ishani Borthakur、Milan Maji、Abhisek Joshi、Sabuj Kundu

  DOI：10.1021/acs.joc.1c02625

  日期：2022.1.7

  Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested

  在这里，我们展示了一种通过借氢 (BH) 方法对叠氮化物/硝基化合物进行还原烷基化的有效方案。通过遵循该协议，在温和且无溶剂的条件下获得了选择性的单烷基化胺和二烷基化胺。进行了一系列对照实验和氘标记实验以了解这一催化过程。机理研究表明，Ir(III)-H 是该反应的活性中间体。KIE 研究表明，酒精的 C-H 键断裂可能是限速步骤。值得注意的是，这种无溶剂策略揭示了大约 5600 的高 TON。基于动力学研究和控制实验，提出了一种金属-配体协同机制。
• Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors
  作者：Elham Babazadeh Rezaei、Fahimeh Abedinifar、Homa Azizian、Mohammad Nazari Montazer、Mehdi Asadi、Samanesadat Hosseini、Saghi Sepehri、Maryam Mohammadi-Khanaposhtani、Mahmood Biglar、Bagher Larijani、Massoud Amanlou、Mohammad Mahdavi

  DOI：10.1007/s11696-021-01653-4

  日期：2021.8

  A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25 µM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14 µM) was the most potent

  合成了一系列新的甲硝唑-1,2,3-三唑衍生物6a-o，并作为幽门螺杆菌脲酶抑制剂进行了评估。所有合成的化合物都比标准抑制剂硫脲对脲酶更有效。在合成的化合物中，化合物 6f (IC50 = 1.975 ± 0.25 µM) 的抑制活性比硫脲 (IC50 = 22.00 ± 0.14 µM) 高 11-fos 左右，是最有效的化合物。该化合物的动力学研究表明，化合物 6f 以非竞争性模式抑制脲酶。基于分子模型研究，化合物 6f 指向双镍中心，并通过 H 键和 T 形 π-π 疏水相互作用与关键残基 His492 和 Asp633 稳定。此外，它通过与His593和Arg609的相互作用锚定在活性位点腔中的螺旋-转角-螺旋基序上。最后，
• Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process
  作者：Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat、Tanita Gettongsong

  DOI：10.1039/c3ob27493d

  日期：——

  4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained

  描述了通过多米诺法方便地合成2，4-未取代的喹啉-3-羧酸乙酯。该合成使用芳基甲基叠氮化物作为前体，该前体经历酸促进的重排以产生N-芳基亚胺鎓离子。继加3-乙氧基丙烯酸乙酯，分子内亲电芳族取代，消除和随后的氧化，喹啉产物以中等至优异的产率获得。