3-((4-(trifluoromethyl)phenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde | 1430118-17-4

• 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-(trifluoromethyl)phenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde
• 英文别名: 3-[2-[4-(Trifluoromethyl)phenyl]ethynyl]-1-benzothiophene-2-carbaldehyde
• CAS: 1430118-17-4
• 化学式: C₁₈H₉F₃OS
• 分子量: 330.33
• InChiKey: OUCVDXYAUYDTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-((4-(trifluoromethyl)phenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde 在 silver nitrate 、 叔丁胺 作用下， 以 乙醇 为溶剂， 反应 55.0h， 以65%的产率得到3-(4-(trifluoromethyl)phenyl)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：

  4-乙炔基-α,α,α-三氟甲苯 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以68%的产率得到3-((4-(trifluoromethyl)phenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction

  摘要：

  An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydorbenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydorbenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of beta-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using L-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-digcyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment.

  DOI：

  10.1021/jo400400c

文献信息

• [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。
• 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
  申请人：Universität Heidelberg

  公开号：EP3328846A1

  公开（公告）日：2018-06-06