2-(but-2-yn-1-yloxy)-3-methoxybenzaldehyde

• 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: 2-(but-2-yn-1-yloxy)-3-methoxybenzaldehyde
• 英文别名: 2-But-2-ynoxy-3-methoxybenzaldehyde
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: YXJNPKZEQCEFTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(but-2-yn-1-yloxy)-3-methoxybenzaldehyde 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 C₁₂H₁₂O₃
  参考文献：
  名称：

  炔烃正式加氢酰化反应中的NHC稳定基团

  摘要：

  目前，正受到N-杂环卡宾（NHC）催化的转化机理的详细研究，针对操作中的活性催化剂以及关键中间体的结构和反应性提出了疑问。这些机理研究的动力是需要了解催化剂体系的细微变化对其反应性的巨大影响，以及阐明经典催化循环中难以捉摸的中间体的情况。在醛的活化过程中，被广泛称为布雷斯洛中间体的烯胺结构的形成被广泛接受。但是，以前我们可以证明，该烯醇除了通过其离子反应途径外，还可以通过与起始原料一起进行氧化还原过程来遵循自由基途径。在本研究中，我们旨在阐明这些自由基途径是否是更普遍的现象，特别是在炔烃的正式加氢酰化反应中。自由基种类的观察以及自由基和离子途径中关键元素步骤的计算分析可能会导致基于NHC稳定碳自由基的化学的进一步发展。

  DOI：

  10.1002/ejoc.201801185
• 作为产物：
  描述：

  邻香草醛 、 1-溴-2-丁炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以98.5%的产率得到2-(but-2-yn-1-yloxy)-3-methoxybenzaldehyde
  参考文献：
  名称：

  通过亚氨基Diels-Alder反应轻松进行一锅区域选择性合成功能化的新型苯并[ f ]铬基[4,3- b ] [1,7]萘啶和苯并[ f ] [1,7]萘啶

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2016.12.050

文献信息

• 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.
• 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.
• NHC‐Stabilized Radicals in the Formal Hydroacylation Reaction of Alkynes
  作者：Jenny Phan、Stephanie‐M. Ruser、Kirsten Zeitler、Julia Rehbein

  DOI：10.1002/ejoc.201801185

  日期：2019.1.23

  Mechanistic details of transformations catalyzed by N‐heterocyclic carbenes (NHC) are currently of great interest, targeting questions on the active catalyst in operation and the structure and reactivity of key intermediates. These mechanistic studies are driven by the need to understand the big impact of subtle changes on the catalyst system on its reactivity, as well as to clarify the situation around

  目前，正受到N-杂环卡宾（NHC）催化的转化机理的详细研究，针对操作中的活性催化剂以及关键中间体的结构和反应性提出了疑问。这些机理研究的动力是需要了解催化剂体系的细微变化对其反应性的巨大影响，以及阐明经典催化循环中难以捉摸的中间体的情况。在醛的活化过程中，被广泛称为布雷斯洛中间体的烯胺结构的形成被广泛接受。但是，以前我们可以证明，该烯醇除了通过其离子反应途径外，还可以通过与起始原料一起进行氧化还原过程来遵循自由基途径。在本研究中，我们旨在阐明这些自由基途径是否是更普遍的现象，特别是在炔烃的正式加氢酰化反应中。自由基种类的观察以及自由基和离子途径中关键元素步骤的计算分析可能会导致基于NHC稳定碳自由基的化学的进一步发展。