3-(phenylethynyl)benzofuran-2-carbaldehyde | 1389315-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(phenylethynyl)benzofuran-2-carbaldehyde
• CAS: 1389315-84-7
• 化学式: C₁₇H₁₀O₂
• 分子量: 246.265
• InChiKey: RGBPNGWVDBFBKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(phenylethynyl)benzofuran-2-carbaldehyde 在 silver nitrate 、 叔丁胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到3-phenylbenzofuro[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-bromobenzofuran-2-carbaldehyde 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以96%的产率得到3-(phenylethynyl)benzofuran-2-carbaldehyde
  参考文献：
  名称：

  A CuBr-mediated aerobic reaction of 2-alkynylbenzaldehydes and primary amines: synthesis of 4-bromoisoquinolones

  摘要：

  一种从2-炔基苯甲醛和初级胺合成4-溴异喹啉的方法已被开发，该反应在氧气氛围下由CuBr介导，其中CuBr在促进这些反应中扮演多重角色。

  DOI：

  10.1039/c2cc33426g

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。
• 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。
• 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...