2‐(3,4,5‐trimethoxyphenylethynyl)benzaldehyde | 437611-93-3

• 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‐(3,4,5‐trimethoxyphenylethynyl)benzaldehyde
• 英文别名: 2-(2-(3,4,5-trimethoxyphenyl)ethynyl)benzaldehyde；2-(3,4,5-trimethoxyphenylethynyl)benzaldehyde
• CAS: 437611-93-3
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: SEGKMQBLFXQRQF-UHFFFAOYSA-N

物化性质

• 熔点：
  139-142 °C
• 沸点：
  460.5±45.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2‐(3,4,5‐trimethoxyphenylethynyl)benzaldehyde 在 silver nitrate 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 3-(3,4,5-trimethoxyphenyl)isoquinoline
  参考文献：
  名称：

  通过亚氨基炔的亲电环化合成取代的异喹啉。

  摘要：

  邻-（1-炔基）苯甲醛和类似的吡啶甲醛的叔丁基亚胺已在I（2），ICl，PhSeCl，PhSCl和pO（2）NC（6）H（ 4）SCl分别得到相应的含卤素，硒和硫的二取代异喹啉和萘啶。该方法可容纳各种亚氨基炔，并以中等至极好的收率提供预期的杂环。通过这些相同的亚氨基炔的金属催化的闭环合成了单取代的异喹啉和萘啶。银催化的闭环在50摄氏度下将芳基，烯基和烷基取代的亚氨基炔烃环化方面非常有效。

  DOI：

  10.1021/jo020020e
• 作为产物：
  描述：

  5-(2,2-dibromovinyl)-1,2,3-trimethoxybenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.67h， 生成 2‐(3,4,5‐trimethoxyphenylethynyl)benzaldehyde
  参考文献：
  名称：

  Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

  摘要：

  Under Sc(OTf)(3) catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp(3)-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.007

文献信息

• Gold‐Catalyzed One‐Pot A ³ ‐Coupling/1,5‐Hydride Shift/Schmittel‐Type Cyclization: From Aldehydes, Amines and Alkynes to the Synthesis of Benzo[ <i>b</i> ]fluorenes
  作者：Danilo M. Lustosa、Deborah Hartmann、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/ejoc.201901906

  日期：2020.3.8

  A short cut to anellated systems by gold catalysis is based on a combination of a gold‐catalyzed A3‐coupling followed by a 1,5‐hydride shift and a Schmittel‐type cyclization in a single synthetic operation.

  通过单次合成操作将金催化的A 3偶联，随后的1,5氢化物转变和Schmittel型环化相结合，是通过金催化对带芳构体系的捷径。
• A gold(<scp>i</scp>)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes
  作者：Wei Fang、Yin Wei、Min Shi

  DOI：10.1039/c7cc07042j

  日期：——

  moderate to good yields. The further transformations as well as application of the product have been presented and a plausible reaction mechanism has been also proposed on the basis of deuterium labeling and control experiments.

  一种新颖的金（I）催化的邻（芳基乙炔基）亚芳基亚甲基环丙烷的分子串联串联环化反应提供了一种以中等到良好的产率制备官能化的11H-苯并[a]芴衍生物的有效方法。在氘标记和对照实验的基础上，提出了产物的进一步转化及其应用，并提出了合理的反应机理。
• Regio- and Stereoselective Construction of Highly Functionalized 3-Benzazepine Skeletons through Ring-Opening Cycloamination Reactions Catalyzed by Gold
  作者：Xiangwei Du、Shuang Yang、Jingyu Yang、Yuanhong Liu

  DOI：10.1002/chem.201002502

  日期：2011.4.26

  Ring size under control: Highly functionalized 1‐amino‐ or 1‐hydroxy‐1H‐benzo[d]azepines have been prepared through a gold‐catalyzed cyclization of (o‐alkynyl)phenyl aziridines with heteronucleophiles. After removal of the phthalimido group, the products can be further transformed into 1H‐benzo[d]azepin‐1‐ones (see scheme; IBX=2‐iodoxybenzoic acid, Phth=pthalimido).

  环的大小受到控制：高功能化的1-氨基或1-羟基-1 H-苯并[ d ]氮杂环庚烷是通过（o-炔基）苯基氮丙啶与杂多亲核试剂的金催化环化反应制备的。除去邻苯二甲酰亚胺基团后，可以将产物进一步转化为1 H-苯并[ d ] azepin-1-酮（参见方案； IBX = 2-碘氧基苯甲酸，Phth =邻苯二甲酰亚胺）。
• Phosphoramidates as Transient Precursors of Nitrogen‐Centered Radical Under Visible‐Light Irradiation: Application to the Synthesis of Phthalazine Derivatives
  作者：Maxime De Abreu、Mohamed Selkti、Philippe Belmont、Etienne Brachet

  DOI：10.1002/adsc.202000018

  日期：2020.5.26

  N‐Centered Radical (NCR) precursors under visible‐light irradiation. More precisely among this class of phosphorus‐derived compounds, we studied the radical reactivity of phosphonohydrazones, under mild reaction conditions, which allowed the synthesis of a wide and diversified library of the scarcely reported phthalazine scaffold. Mechanistic investigations confirmed the formation of a NCR from these brand‐new

  磷酰胺盐首次在可见光照射下作为有效的N中心自由基（NCR）前体出现。更确切地说，在这类磷衍生化合物中，我们研究了膦酰hydr在温和的反应条件下的自由基反应性，从而可以合成一个鲜为人知的邻苯二甲酰胺骨架的宽泛且多样化的文库。机理研究证实，这些全新的膦酰hydr （衍生自氨基磷酸酯）形成了NCR，它们进一步参与了分子内6- exo- dig环化反应以提供酞嗪。与其他预活化部分相比，氨基磷酸酯基团是自消灭的，因此增强了其对C-N键形成的吸引力。
• Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of <i>ortho</i>-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene Derivatives
  作者：Gaëlle Mariaule、Gregory Newsome、Patrick Y. Toullec、Philippe Belmont、Véronique Michelet

  DOI：10.1021/ol5021256

  日期：2014.9.5

  A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).