3-((4-methoxyphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde | 1401716-02-6

• 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: 3-((4-methoxyphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde
• 英文别名: 3-[2-(4-Methoxyphenyl)ethynyl]-1-benzothiophene-2-carbaldehyde
• CAS: 1401716-02-6
• 化学式: C₁₈H₁₂O₂S
• 分子量: 292.358
• InChiKey: JORBAWKXQLLIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((4-methoxyphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde 在 silver nitrate 、 叔丁胺 作用下， 以 氘代甲醇-d 为溶剂， 反应 40.0h， 以64%的产率得到4D-3-(4-methoxyphenyl)benzo[4,5]thieno[2,3-c]pyridine
  参考文献：
  名称：

  Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

  摘要：

  An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a-t and benzofuropyridines 8a-p by the reaction of o-alkynyl aldehyde 4a-t and 5a-p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excellent yields under mild and environmentally friendly reaction conditions with excellent regioselectivity. The developed chemistry has been successfully extended for the selective synthesis of C-4 deuterated benzothienopyridines 7u-v and benzofurop-yridines 8q-r. The role of the ethanolic proton in the reaction was validated by deuterium-labeling experiments.

  DOI：

  10.1021/acs.joc.5b01647
• 作为产物：
  描述：

  3-溴苯并噻吩-2-甲醛 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 copper(l) iodide 作用下， 反应 0.08h， 以92%的产率得到3-((4-methoxyphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde
  参考文献：
  名称：

  金催化的噻吩系二炔的正式环化/二聚

  摘要：

  已经发现了噻吩系二炔的双重金催化反应的新途径。通过正式的环化/二聚顺序，获得了一系列完全共轭的炔基取代的苯并噻吩和苯并呋喃。由于它们的共轭作用，所有产品都是荧光的。已经进行了机理研究，表明乙炔金参与了该转变。

  DOI：

  10.1002/chem.201700061

文献信息

• Silver-catalyzed regioselective synthesis of acridines, quinolines, and naphthalenes from 3-(2-alkynyl)aryl-β-ketoesters
  作者：Satya Prakash Shukla、Rakesh Tiwari、Akhilesh Kumar Verma

  DOI：10.1016/j.tet.2012.08.068

  日期：2012.11

  general synthetic method for a wide range of medicinally useful 2-carboxylate derivatives of acridinols, quinolinols, and naphthalenols has been developed via silver-catalyzed electrophilic cyclization of 3-(2-alkynyl)aryl-β-ketoesters. The designed reaction involved selective C–C bond formation on more electrophilic alkynyl carbon, which resulted in the regioselective 6-endo-dig cyclized product, as confirmed

  通过银催化的3-（2-炔基）芳基-β-酮酸酯的亲电子环化反应，已经开发了一种简便，有效且通用的合成方法，用于各种医学上有用的a啶醇，喹啉醇和萘酚的2-羧酸酯衍生物。所设计的反应涉及在多个电子炔基碳选择性C-C键的形成，这就造成了区域选择性6-内-挖环化产物，通过X射线晶体学研究证实。进行氘标记实验以支持所提出的机制。合成方法可适应炔烃上广泛的官能团变异，这对结构和生物活性评估非常有利。
• Dual function of carbon tetrachloride: synthesis of chlorinated heterocycles
  作者：Shiv Kumar、Rakesh K. Saunthwal、Kapil M. Saini、Akhilesh K. Verma

  DOI：10.1039/c9cc04746h

  日期：——

  An efficient tandem approach to invent highly chlorinated and structurally diversified dihydropyridine fused heterocycles from easily accessible ortho-alkynylaldehydes and primary amines under metal-free conditions via four sequential bond formations is described. The proposed tandem route proceeds via a carbon tetrachloride-mediated 6-endo-dig ring closure followed by nucleophilic attack of the trichloromethyl

  描述了一种有效的串联方法，该方法可在无金属条件下通过四个连续的键形成方法，从容易获得的邻炔基乙醛和伯胺中发明高度氯化且结构多样的二氢吡啶稠合杂环。所提出的串联途径是通过四氯化碳介导的6-内切开环闭合，随后是对三氯甲基阴离子的亲核攻击。
• Ag^I-Catalyzed Cascade Strategy: Regioselective Access to Diversely Substituted Fused Benzimidazo[2,1-<i>a</i>]isoquinolines, Naphthyridines, Thienopyridines, and Quinoxalines in Water
  作者：Vineeta Rustagi、Rakesh Tiwari、Akhilesh Kumar Verma

  DOI：10.1002/ejoc.201200546

  日期：2012.8

  bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig cyclized products in good to excellent yields. The proposed mechanistic pathway for the synthesis of fused heterocycles proceeding through formation of ring A prior to ring B, which formed through a second intramolecular attack of the nitrogen onto the alkynyl carbon, was supported by mechanistic experiments

  一种环境友好且操作简单的一锅法，用于在水中使用 AgI 作为催化剂从邻炔醛和芳胺中区域选择性串联合成多种取代的稠合苯并咪唑并 [2,1-a] 异喹啉、萘啶、噻吩并吡啶和喹喔啉被描述。该反应显示在更具亲电性的炔基碳上形成了选择性的 N-C 键，从而产生了区域选择性的 6-endo-dig 环化产物，产率很好。所提出的合成稠合杂环的机理途径是在环 B 之前形成环 A，环 B 是通过氮对炔基碳的第二次分子内攻击形成的，得到了分离的中间体 U 和环化产物 5a 的机械实验和 X 射线晶体学研究的支持。对比实验表明，分子内亲核攻击的可行性高于外部亲核试剂的分子间攻击。这种催化的绿色方案已有效地应用于水中的双串联环化。
• [EN] NOVEL COMPOUNDS EXHIBITING PHOTOPHYSICAL PROPERTIES UPON FORMATION OF LEWIS ACID-BASE ADDUCTS USING NON-CHELATING BORANES, METHOD FOR PRODUCING THE SAME AND DEVICES INCLUDING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS PRÉSENTANT DES PROPRIÉTÉS PHOTOPHYSIQUES LORS DE LA FORMATION DE PRODUITS D'ADDITION D'ACIDE-BASE DE LEWIS À L'AIDE DE BORANES NON CHÉLATANTS, PROCÉDÉ POUR LEUR PRODUCTION ET DISPOSITIFS LES COMPRENANT
  申请人：UNIVERSITÄT HEIDELBERG

  公开号：WO2017016653A1

  公开（公告）日：2017-02-02

  The present invention relates to novel compounds exhibiting photophysical properties upon formation of Lewis acid-base adducts using non-chelating boranes and methods for producing the same as well as devices that include such Lewis acid-base adducts of the following general formula (I).

  本发明涉及使用非螯合硼烷形成Lewis酸-碱加合物的新化合物，以及制备这些化合物的方法，以及包括以下一般式(I)的Lewis酸-碱加合物的器件。
• Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(<scp>iii</scp>)-catalyzed regioselective 6-endo-dig ring closure
  作者：Rajeev R. Jha、Rakesh K. Saunthwal、Akhilesh K. Verma

  DOI：10.1039/c3ob42035c

  日期：——

  An operationally simple approach for the stereoselective tandem synthesis of novel thiazolo fused naphthyridines 5a–o and thienopyridines 8a–e by the reaction of o-alkynylaldehydes with L-cystine methyl ester hydrochloride via Au(III)-catalyzed regioselective 6-endo-dig ring closure under mild reaction conditions is described. It is noteworthy that alkynes bearing an alkyl and a strong electron-withdrawing nitro group successfully afforded the desired products in good yields.

  本研究介绍了一种操作简单的方法，即在温和的反应条件下，通过 Au(III) 催化的区域选择性 6-endo-dig 封环反应，使邻炔醛与 L-胱氨酸甲酯盐酸盐发生反应，从而立体选择性地串联合成新型噻唑并萘啶 5a-o 和噻吩并吡啶 8a-e。值得注意的是，带有一个烷基和一个强夺电子硝基的炔烃成功地以良好的收率得到了所需的产物。