4-(azidomethyl)-6-chloro-2H-chromen-2-one | 1217436-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(azidomethyl)-6-chloro-2H-chromen-2-one
• 英文别名: 4-azidomethyl-6-chloro-chromen-2-one；4-(Azidomethyl)-6-chlorochromen-2-one
• CAS: 1217436-24-2
• 化学式: C₁₀H₆ClN₃O₂
• 分子量: 235.63
• InChiKey: IJINUXVYAPABQE-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(azidomethyl)-6-chloro-2H-chromen-2-one 、 tert-butyl 4-((prop-2-ynylthio)carbonothioyl)piperazine-1-carboxylate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以85%的产率得到tert-butyl 4-((((1-((6-chloro-2-oxo-2H-chromen-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)thio)carbonothioyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of coumarin–1,2,3-triazole–dithiocarbamate hybrids as potent LSD1 inhibitors

  摘要：

  将新型香豆素-1,2,3-三唑-二硫代氨基甲酸酯混合物设计为强效LSD1抑制剂，通过引入香豆素骨架。

  DOI：

  10.1039/c4md00031e
• 作为产物：
  描述：

  6-氯-4-(氯甲基)-2H-色烯-2-酮 在 sodium azide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以89%的产率得到4-(azidomethyl)-6-chloro-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of coumarin–1,2,3-triazole–dithiocarbamate hybrids as potent LSD1 inhibitors

  摘要：

  将新型香豆素-1,2,3-三唑-二硫代氨基甲酸酯混合物设计为强效LSD1抑制剂，通过引入香豆素骨架。

  DOI：

  10.1039/c4md00031e

文献信息

• Click chemistry approach for the regioselective synthesis of iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles and their photophysical properties
  作者：Ashish Anand、Manohar V. Kulkarni

  DOI：10.1080/00397911.2017.1283524

  日期：2017.4.3

  ABSTRACT Copper-catalyzed reaction of N-propargyl isoindoline-1,3-dione and 4-azidomethyl coumarins / 4-azidomethyl-1-aza coumarins under click chemistry conditions afforded 1,4-disubstituted 1,2,3-triazoles, whereas ruthenium catalysis yielded isomeric 1,5-disubstituted 1,2,3-triazoles. The two regioisomers have been distinguished by NOE studies. UV absorption for a given pair of isomers exhibited

  摘要 在点击化学条件下，N-炔丙基异吲哚啉-1,3-二酮和 4-叠氮甲基香豆素/4-叠氮甲基-1-氮杂香豆素在铜催化下反应得到 1,4-二取代 1,2,3-三唑，而钌催化产生异构的 1,5-二取代的 1,2,3-三唑。两种区域异构体已通过 NOE 研究区分开来。一对给定异构体的紫外吸收显示出相似的趋势，而荧光测量显示出相当大的差异。还对叠氮化物与铜和钌的相互作用进行了光物理研究。图形概要
• Cu (I) Catalyzed One Pot S_N -Click Reactions of Halogenated Coumarins and 1-<i>aza</i> -coumarins
  作者：Hrishikesh M. Revankar、Manohar V. Kulkarni

  DOI：10.1002/jhet.3090

  日期：2018.2

  A one pot three component, copper catalyzed azide‐alkyne cycloaddition reaction has been employed for the synthesis of bis‐coumarinyl triazoles (A–D) using 4‐chloro, 4‐bromomethyl, 3‐bromoacetyl and 4‐bromomethyl‐1‐aza‐coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.

  一锅三组分，铜催化的叠氮化物-炔烃环加成反应已经用于合成双-coumarinyl三唑（甲- d）使用4-氯，4-溴甲基，3-溴乙酰和4-溴甲基- 1-氮杂-香豆素（I – IV），叠氮化钠和香豆素炔丙基醚（V – IX）产量适中。
• Click chemistry based regioselective one‐pot synthesis of coumarin‐3‐yl‐methyl‐1,2,3‐triazolyl‐1,2,4‐triazol‐3(4 <i>H</i> )‐ones as newer potent antitubercular agents
  作者：Shilpa M. Somagond、Ravindra R. Kamble、Praveen K. Bayannavar、Saba Kauser J. Shaikh、Shrinivas D. Joshi、Vijay M. Kumbar、Aravind R. Nesaragi、Mahadevappa Y. Kariduraganavar

  DOI：10.1002/ardp.201900013

  日期：2019.10

  Coumarin‐3‐yl‐methyl‐1,2,3‐triazolyl‐1,2,4‐triazol‐3(4H)‐ones (8k‐z) were synthesized via copper(I)‐catalyzed azide‐alkyne cycloaddition click chemistry. The synthesized hybrid molecules were characterized by spectral studies. Compounds 8k‐z were screened for their in vitro anti‐TB activity by using the Microplate Alamar Blue assay and for cytotoxicity using the MTT assay. Some of the compounds were

  香豆素-3-基-甲基-1,2,3-三唑基-1,2,4-三唑-3（4H）-酮（8k-z）是通过铜（I）催化的叠氮化物-炔环加成点击化学合成的. 合成的杂化分子通过光谱研究表征。使用 Microplate Alamar Blue 测定法筛选化合物 8k-z 的体外抗结核活性，并使用 MTT 测定法筛选其细胞毒性。发现其中一些化合物对测试的结核分枝杆菌 H37Rv 菌株最有效，MIC 为 1.60 µg/ml。此外，将化合物对接到 InhA 结合口袋中显示出强烈的结合相互作用，并记录了有效的总体对接分数。分别使用 Molinspiration 和 Protox 计算药物相似性和毒性研究。
• Unusual anisotropic effects from 1,3-dipolar cycloadducts of 4-azidomethyl coumarins
  作者：Raviraj A. Kusanur、Manohar V. Kulkarni、Geetha M. Kulkarni、Susanta K. Nayak、Tayur N. Guru Row、Kilivelu Ganesan、Chung-Ming Sun

  DOI：10.1002/jhet.273

  日期：——

  acetone to give 4-azidomethylcoumarins (), which underwent 1,3-dipolar cycloaddition with acetylenic dipolarophiles to give triazoles (). These triazoles () have been found to exhibit interesting variations in the chemical shifts of C3H and C4-methylene protons. Protonation studies indicate that the shielding effect of the C3H of coumarin is due to π-electrons of the triazole ring, further supported

  4-溴甲基香豆素（）与 丙酮水溶液中的叠氮化钠制得4-叠氮甲基香豆素（），然后与炔属双极性亲和剂进行1,3-偶极环加成反应，得到三唑（）。这些三唑业已发现）在C 3 H和C 4-亚甲基质子的化学位移方面表现出有趣的变化。质子化研究表明，香豆素C 3 H的屏蔽作用归因于三唑环的π电子，这进一步受到衍射和计算研究的支持。J.杂环化​​学.2010。
• Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity
  作者：Reshma J. Naik、Manohar V. Kulkarni、K. Sreedhara Ranganath Pai、Pawan G. Nayak

  DOI：10.1111/j.1747-0285.2012.01441.x

  日期：2012.10

  1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a–m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2H‐chromen‐2‐ones 3a–m. The intermediate azides 4a–m underwent a regioselective 1,3‐dipolar cycloaddition with a 2H‐chromen‐2‐one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n‐butanol reaction medium. Three compounds 5h–j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram‐positive and Gram‐negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.