(E)-3-(benzo[b]thiophen-3-yl)acrylaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (E)-3-(benzo[b]thiophen-3-yl)acrylaldehyde
• 英文别名: (E)-3-(Benzo[b]thiophen-3-yl)acrylaldehyde；(E)-3-(1-benzothiophen-3-yl)prop-2-enal
• 化学式: C₁₁H₈OS
• 分子量: 188.25
• InChiKey: DSSWWKXSSYBFMR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(benzo[b]thiophen-3-yl)acrylaldehyde 在 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (E)-N-(3-(benzo[b]thiophen-3-yl)allyl)aniline
  参考文献：
  名称：

  分子内狄尔斯-阿尔德乙烯基芳烃（IMDAV）反应在苯并、碳环、噻吩并噻吩异吲哚甲酸合成中的应用及其局限性

  摘要：

  噻吩基烯丙胺很容易从相应的噻吩基醛中获得，与马来酸酐和三氟甲基马来酸酐反应，形成具有噻吩并[2,3- f ]异吲哚核心的酸。该反应序列涉及两个连续步骤：初始烯丙胺的氮原子的酰化和分子内狄尔斯-阿尔德乙烯基芳烃（IMDAV）反应。对所提出方法的范围和局限性进行了彻底研究。借助X射线分析和DFT计算表明，关键步骤IMDAV反应通过外过渡态进行，导致目标杂环的单一非对映异构体的排他性形成。所获得的功能取代的噻吩并[2,3- f ]异吲哚羧酸是用于进一步转化和生物筛选的潜在有用底物。对所得化合物的抗菌评估表明，1-氧代-2-(3-(三氟甲基)苯基)六氢苯并[4,5]噻吩并[2,3- f ]异吲哚-10-甲酸是该化合物中活性最高的样品。合成文库。它对金黄色葡萄球菌、屎肠球菌、蜡样芽孢杆菌、藤黄微球菌等敏感的革兰氏阳性菌以及大肠杆菌、荧光假单胞菌等革兰氏阴性菌具有抗菌活性，MIC值范围为4～ 64μg·mL

  DOI：

  10.1039/d3ob01933k
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 三乙胺 在 indium(III) triflate 、 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到(E)-3-(benzo[b]thiophen-3-yl)acrylaldehyde
  参考文献：
  名称：

  Rare Earth Triflates/Chlorotrimethylsilane-Promoted One-Pot Synthesis of Enals

  摘要：

  Some heteroaromatic aldehydes were subjected to conditions promoting the rare earth triflates/chlorotrimethylsilane-promoted one-pot synthesis of enals. As a result, diverse alpha,beta-unsaturated aldehydes were obtained in moderate yields.

  DOI：

  10.3987/com-13-s(s)98

文献信息

• Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3‐Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
  作者：Marvin Stephan、Jesco Panther、Fabio Wilbert、Pauline Ozog、Thomas J. J. Müller

  DOI：10.1002/ejoc.202000066

  日期：2020.4.16

  The Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using CataCXium® Ptb as a ligand, NaHCO3 as a base, and nBu4NCl provides an efficient access to 3‐(hetero)aryl propenals/propenones, which are directly employed in consecutive multicomponent syntheses of pyrazoles in a one‐pot fashion.

  使用CataCXium®Ptb作为配体，NaHCO 3作为碱和n Bu 4 NCl进行（杂）芳基溴化物和丙烯醛或乙烯基酮的Heck反应，可以有效地获得3-（杂）芳基丙烯/丙烯酮。以单罐方式直接用于吡唑的连续多组分合成中。
• ANTICANCER 1,3-DIOXANE-4,6-DIONE DERIVATIVES AND METHOD OF COMBINATORIAL SYNTHESIS THEREOF
  申请人：National Guard Health Affairs

  公开号：US20200290975A1

  公开（公告）日：2020-09-17

  Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

  芳基亚甲基-1,3-二氧杂环己-4,6-二酮的化合物、合成方法和癌症治疗方法。基于梅尔德鲁姆酸的化学和混合固-液方法。该方法包括对酮和醛组分进行保护并同时固相固定，引入适用于保护的取代基、嫁接和衍生物，分离和恢复活性羰基反应性，将酮库与马隆酸酯反应，将产物与液相中的醛库反应，通过制备性高效液相色谱法分离产物。
• Influence of the catalytic conditions on the selectivity of the Pd-catalyzed Heck arylation of acrolein derivatives
  作者：Sébastien Noël、Laurent Djakovitch、Catherine Pinel

  DOI：10.1016/j.tetlet.2006.03.186

  日期：2006.6

  The Heck arylation of acrolein with a variety of condensed aryl and heteroaryl halides is described. Depending on the substrate, up to 87% isolated yield to the expected aldehydes was achieved. When the reaction was run on diethylacetal acrolein, the choice of catalytic system dramatically affected the selectivity of the reaction: the catalyst system based on Herrmann’s palladacycle complex gave mainly

  描述了丙烯醛与各种缩合的芳基和杂芳基卤化物的Heck芳基化反应。取决于底物，获得了高达87％的预期醛分离产率。当反应在二乙缩醛丙烯醛上进行时，催化体系的选择极大地影响了反应的选择性：基于Herrmann的palladacycle配合物的催化剂体系主要产生饱和酯2，而Cacchi的条件导致形成α，β-不饱和醛1。
• Efficient Heterogeneously Palladium-Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydesor 3-Arylpropionic Esters
  作者：Sébastien Noël、Ciahong Luo、Catherine Pinel、Laurent Djakovitch

  DOI：10.1002/adsc.200600593

  日期：2007.5.7

  A heterogeneous tetrakis(ammine)palladium-NaY zeolite [Pd(NH3)4]/NaY} catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck

  使用多种芳基和杂芳基溴化物，成功地将异质四（氨）钯-NaY沸石[Pd（NH 3）4 ] / NaY}催化剂用于丙烯醛二乙缩醛的Heck芳基化反应。取决于反应条件（Heck与分别获得了对3-芳基丙酸酯或对肉桂醛具有良好至高选择性的Cacchi。在经典的Heck条件下，虽然发现催化剂在前两次运行中都稳定，但从第三次循环开始就显示出明显的活性损失。在卡奇条件下，催化剂不能重复使用，因为它会导致高脱卤率。所有结果表明反应通过本体溶液中溶解的钯物质进行（浸出）。如通过透射电子显微镜（TEM）分析所观察到的，虽然这些物种可以在Heck条件下被沸石骨架捕获并稳定，但它们在Cacchi条件下倾向于形成大的钯（0）聚集体，从而导致脱卤而不是预期的颈耦合。
• Anticancer 1,3-dioxane-4,6-dione derivatives and method of combinatorial synthesis thereof
  申请人：National Guard Health Affairs

  公开号：US11161823B2

  公开（公告）日：2021-11-02

  Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

  芳基-1,3-二恶烷-4,6-二酮的化合物、合成方法和癌症治疗方法。一种基于 Meldrum 酸的化学和固液混合法。该方法包括保护酮和醛成分并同时固定在固相上，引入与保护、分离和恢复活性羰基反应性兼容的取代基、接枝和衍生物，酮库与丙二酸酯反应，产物与液相中的醛库反应，以及通过制备型高效液相色谱分离产物。