5-bromo-2-(but-2-ynyloxy)benzaldehyde | 1248410-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-2-(but-2-ynyloxy)benzaldehyde
• 英文别名: 5-bromo-2-(but-2-yn-1-yloxy)benzaldehyde；5-Bromo-2-but-2-ynoxybenzaldehyde
• CAS: 1248410-67-4
• 化学式: C₁₁H₉BrO₂
• 分子量: 253.095
• InChiKey: KWKRIAGAHHVMOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(but-2-ynyloxy)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-benzyl-1-(5-bromo-2-(but-2-yn-1-yloxy)phenyl)methanamine
  参考文献：
  名称：

  氨基苯甲酸胺的亲核加成反应：邻（烷氧基）苄胺向1,3-苯并恶嗪的环化反应

  摘要：

  报道了一种新的钌催化的邻-（炔氧基）苄胺成环化成二氢-1,3-苯并恶嗪的环化反应。据认为，环化反应是通过乙烯基钌卡宾中间体进行的，该中间体容易由[Cp * RuCl（cod）]和N 2 CHSiMe 3形成。温和的反应条件和高效的程序使您可以轻松制备各种新型的2-乙烯基-2-取代的1,3-苯并恶嗪衍生物。将原料中的内部C（sp）重排为最终的1,3-苯并恶嗪中的四取代的C（sp 3）原子非常引人注目。

  DOI：

  10.1002/anie.201410284
• 作为产物：
  描述：

  1-溴-2-丁炔 、 5-溴水杨醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 5-bromo-2-(but-2-ynyloxy)benzaldehyde
  参考文献：
  名称：

  氨基苯甲酸胺的亲核加成反应：邻（烷氧基）苄胺向1,3-苯并恶嗪的环化反应

  摘要：

  报道了一种新的钌催化的邻-（炔氧基）苄胺成环化成二氢-1,3-苯并恶嗪的环化反应。据认为，环化反应是通过乙烯基钌卡宾中间体进行的，该中间体容易由[Cp * RuCl（cod）]和N 2 CHSiMe 3形成。温和的反应条件和高效的程序使您可以轻松制备各种新型的2-乙烯基-2-取代的1,3-苯并恶嗪衍生物。将原料中的内部C（sp）重排为最终的1,3-苯并恶嗪中的四取代的C（sp 3）原子非常引人注目。

  DOI：

  10.1002/anie.201410284

文献信息

• Zirconium oxide (NP) - ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes
  作者：Saeed Balalaie、Ali Poursaeed、Malihe Javan Khoshkholgh、Hamid Reza Bijanzadeh、Eckardt Wolf

  DOI：10.1016/j.crci.2011.12.002

  日期：2012.4

  Immobilized ZrO 2 -nanopowder (NP) in ionic liquid and different organic solvents was used as a suitable Lewis-acid for the synthesis of polycyclic heterocycles which contains pyran-based skeletons. Reaction of O -propargylated salicylaldehyde with active methylene compounds in the presence of ZrO 2 -NP in ionic liquid proceeds via domino Knoevenagel hetero Diels-Alder reaction of unactivated alkynes

  摘要 以离子液体和不同有机溶剂中的固定化ZrO 2 -纳米粉体(NP)作为合适的路易斯酸，用于合成含有吡喃基骨架的多环杂环。在离子液体中，在 ZrO 2 -NP 存在下，O-炔丙基化水杨醛与活性亚甲基化合物的反应通过未活化炔烃的多米诺 Knoevenagel 杂 Diels-Alder 反应进行，以构建吡喃骨架。与不同离子液体和有机溶剂的比较表明，1-丁基-3-甲基咪唑硝酸盐[bmim][NO 3 ]反应时间短，收率高，效果最好。在这些条件下进行反应具有收率高、反应时间短和易于后处理等优点。
• A facile one-pot regioselective synthesis of functionalized novel benzo[f]chromeno[4,3-b][1,7]naphthyridines and benzo[f][1,7]naphthyridines via an imino Diels-Alder reaction
  作者：Sateesh Kumar Arepalli、Byeongwoo Park、Jae-Kyung Jung、Kiho Lee、Heesoon Lee

  DOI：10.1016/j.tetlet.2016.12.050

  日期：2017.2

  A novel series of functionalized 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 1,3-diphenylbenzo[f][1,7]naphthyridines have been synthesized by an efficient regioselective one-pot multicomponent synthesis through intra and intermolecular imino Diels-Alder reaction. In this method, we have achieved complete regioselectivity and atom economy with polysubstituted core motifs in moderate to good yields

  通过有效的区域选择性单-羟基合成了一系列新的功能化的13 H-苯并[ f ]铬基[ 4,3- b ] [1,7]萘啶和1,3-二苯并[ f ] [1,7]萘啶通过分子内和分子间亚氨基Diels-Alder反应合成多组分。在这种方法中，我们以中等至良好的产率实现了具有多取代核心基序的完全区域选择性和原子经济性。还讨论了该反应的提议机理。
• Intramolecular Heterocyclization of <i>O</i>-Propargylated Aromatic Hydroxyaldehydes as an Expedient Route to Substituted Chromenopyridines under Metal-Free Conditions
  作者：Selbi Keskin、Metin Balci

  DOI：10.1021/acs.orglett.5b00067

  日期：2015.2.20

  A concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by reaction with propargylamine. The intramolecular cycloaddition reaction between the alkyne and azadiene, which is formed as an intermediate, furnished the desired skeletons.
• Nucleophilic Addition of Amines to Ruthenium Carbenes:<i>ortho</i>-(Alkynyloxy)benzylamine Cyclizations towards 1,3-Benzoxazines
  作者：Carlos González-Rodríguez、José Ramón Suárez、Jesús A. Varela、Carlos Saá

  DOI：10.1002/anie.201410284

  日期：2015.2.23

  ortho‐(alkynyloxy)benzylamines to dihydro‐1,3‐benzoxazines is reported. The cyclization is thought to take place via the vinyl ruthenium carbene intermediates which are easily formed from [Cp*RuCl(cod)] and N2CHSiMe3. The mild reaction conditions and the efficiency of the procedure allow the easy preparation of a broad range of new 2‐vinyl‐2‐substituted 1,3‐benzoxazine derivatives. Rearrangement of

  报道了一种新的钌催化的邻-（炔氧基）苄胺成环化成二氢-1,3-苯并恶嗪的环化反应。据认为，环化反应是通过乙烯基钌卡宾中间体进行的，该中间体容易由[Cp * RuCl（cod）]和N 2 CHSiMe 3形成。温和的反应条件和高效的程序使您可以轻松制备各种新型的2-乙烯基-2-取代的1,3-苯并恶嗪衍生物。将原料中的内部C（sp）重排为最终的1,3-苯并恶嗪中的四取代的C（sp 3）原子非常引人注目。
• Development of 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors
  作者：Sateesh Kumar Arepalli、Chaerim Lee、Seongrak Sim、Kiho Lee、Hyunji Jo、Kyu-Yeon Jun、Youngjoo Kwon、Jong-Soon Kang、Jae-Kyung Jung、Heesoon Lee

  DOI：10.1016/j.bmc.2018.09.019

  日期：2018.10

  A novel series of 35 angularly fused pentacyclic 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridin-5-ium chlorides were designed and synthesized. Their cytotoxic activities were investigated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Among all screened compounds; 28, 30, 34, 35, 46, 48, 52, and 53 compounds exhibited potent cytotoxic activities against all tested human cancer cell lines. Further, these potent lead cytotoxic agents were evaluated against human Topoisomerase I and II alpha inhibition. Among them, the compound 48 exhibited dual Topoisomerase I and II alpha inhibition especially at 20 mu M concentrations the compound 48 exhibited 1.25 times more potent Topoisomerase II alpha inhibitory activity (38.3%) than the reference drug etoposide (30.6%). The compound 52 also exhibited excellent (88.4%) topoisomerase I inhibition than the reference drug camptothecin (66.7%) at 100 mu M concentrations. Molecular docking studies of the compounds 48 and 52 with topo I discovered that they both intercalated into the DNA single-strand cleavage site where the compound 48 have van der Waals interactions with residues Arg364, Pro431, and Asn722 whilst the compound 52 have with Arg364, Thr718, and Asn722 residues. Both the compounds 48 and 52 have pi-pi stacking interactions with the stacked DNA bases. The docking studies of the compound 48 with topo IIa explored that it was bound to the topo II alpha DNA cleavage site where etoposide was situated. The benzo[f]chromeno[4,3-b][1,7]naphthyridine ring of the compound 48 was stacked between the DNA bases of the cleavage site with pi-pi stacking interactions and there were no hydrogen bond interactions with topo II alpha.