3-(phenylethynyl)benzo[b]thiophene-2-carbaldehyde

• 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-(phenylethynyl)benzo[b]thiophene-2-carbaldehyde
• 英文别名: 3-(2-Phenylethynyl)-1-benzothiophene-2-carbaldehyde；3-(2-phenylethynyl)-1-benzothiophene-2-carbaldehyde
• 化学式: C₁₇H₁₀OS
• 分子量: 262.332
• InChiKey: SEOSADFPGKIUMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  3-(phenylethynyl)benzo[b]thiophene-2-carbaldehyde 在 C₅₇H₇₅Au₂N₄⁽¹⁺⁾*C₂F₆NO₄S₂^(1-) 、 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 2-phenyl-4-((3-(phenylethynyl)benzo[b]thiophen-2-yl)ethynyl)dibenzo[b,d]thiophene
  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
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以70%的产率得到3-(phenylethynyl)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

• Synthesis of cyclopentaquinolinone and cyclopentapyridinone from <i>ortho</i>-alkynyl-<i>N</i>-arylaldehyde <i>via</i> superbase-promoted C–N, C–O and C–C bond formation
  作者：Kapil Mohan Saini、Rakesh K. Saunthwal、Sushmita、Akhilesh K. Verma

  DOI：10.1039/d0ob01281e

  日期：——

  and cyclopentapyridinones via C–N, C–C, and CO bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray

  邻炔基醛与伯胺的无环环境友好，无过渡金属，超碱介导的分子内环化反应会通过C–N，C–C和C O键的形成形成高度官能化的氨基取代的环戊喹啉酮和环戊二吡啶酮。与传统的环闭合方法相反，公开了一种不同的环行方式。该方案涉及原位生成亚胺中间体，然后进行氢氧化钾促进的分子内环化反应，随后由二甲基亚砜诱导的脱氢作用导致N杂环的形成。X射线晶体学研究支持氨基稠合的N-杂环的指定结构。
• Access toward Fluorenone Derivatives through Solvent-Free Ruthenium Trichloride Mediated [2 + 2 + 2] Cycloadditions
  作者：Fei Ye、Mansour Haddad、Véronique Michelet、Virginie Ratovelomanana-Vidal

  DOI：10.1021/acs.orglett.6b02840

  日期：2016.11.4

  and practical route for the preparation of highly substituted fluorenones and analogues via solvent-free ruthenium trichloride mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and alkynes has been developed. This green chemistry approach involves a solventless and atom-economical catalytic process to generate densely functionalized fluorenones and related derivatives of high synthetic utility.

  通过无溶剂三氯化钌介导的α，ω-二炔和炔烃的[2 + 2 + 2]环加成反应，开发了一种高效且实用的途径，用于制备高度取代的芴酮和类似物。这种绿色化学方法涉及无溶剂且原子经济的催化过程，以产生具有高合成效用的致密官能化的芴酮和相关衍生物。
• 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。
• [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。
• Metal-free regioselective tandem synthesis of diversely substituted benzimidazo-fused polyheterocycles in aqueous medium
  作者：Pawan K. Mishra、Akhilesh K. Verma

  DOI：10.1039/c6gc02330d

  日期：——

  An operationally simple greener approach for the synthesis of diversely substituted benzimidazo-fused polyheterocycles under the metal-free condition in water has been described. The aqueous medium accelerates the formation of desired...

  已经描述了一种在水中无金属条件下合成多种取代的苯并咪唑稠合的多杂环化合物的操作简单的绿色方法。水性介质可加速所需...