5-fluoro-2-(p-tolyl)benzofuran | 50618-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-fluoro-2-(p-tolyl)benzofuran
• 英文别名: 5-Fluoro-2-(4-methylphenyl)-1-benzofuran
• CAS: 50618-36-5
• 化学式: C₁₅H₁₁FO
• 分子量: 226.25
• InChiKey: SIOWUEBZMDXBNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-(p-tolyl)benzofuran 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 ethyl 4-(5-fluoro 2-benzofuryl) benzyl (2-oxopyrrolidino) phosphinate
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates

  摘要：

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.

  DOI：

  10.1016/0223-5234(93)90084-r
• 作为产物：
  描述：

  ω-(4-Fluorphenoxy)-p-methylacetophenon 生成 5-fluoro-2-(p-tolyl)benzofuran
  参考文献：
  名称：

  Compounds including carboxystyrylphenyl group

  摘要：

  苯并呋喃、苯并噻吩和萘并呋喃，它们被羧基苯乙烯基苯基取代，以及它们对应的酯和酰胺是一种光学增白剂，可用于美白和增亮天然和合成纤维、纸张、树脂等。这些化合物可通过苯并呋喃、苯并噻吩或萘并呋喃与芳香醛或最好是其苯胺衍生物相互作用方便地制备。

  公开号：

  US03974144A1

文献信息

• A concise route to functionalized benzofurans directly from gem-dibromoalkenes and phenols
  作者：Maddali L. N. Rao、Priyabrata Dasgupta

  DOI：10.1039/c5ra13213d

  日期：——

  A tandem strategy for the construction of benzofuran motifs has been developed directly from gem-dibromoalkenes and phenols under palladium-catalyzed conditions.

  已经开发了一种从gem-二溴代烯烃和酚直接在钯催化条件下构建苯并呋喃基团的串联策略。
• Compounds including carboxystyrylphenyl group
  申请人：Sterling Drug Inc.

  公开号：US03974144A1

  公开（公告）日：1976-08-10

  Benzofurans, benzothiophenes, and naphthofurans which are substituted by carboxystyrylphenyl groups and their corresponding esters and amides are optical brightening agents useful for whitening and brightening natural and synthetic fibers, papers, resins and the like. The compounds are conveniently prepared by interacting benzofurans, benzothiophenes or naphthofurans, which are substituted by a p-tolyl group, with an aromatic aldehyde or preferably the anil derivative thereof.

  苯并呋喃、苯并噻吩和萘并呋喃，它们被羧基苯乙烯基苯基取代，以及它们对应的酯和酰胺是一种光学增白剂，可用于美白和增亮天然和合成纤维、纸张、树脂等。这些化合物可通过苯并呋喃、苯并噻吩或萘并呋喃与芳香醛或最好是其苯胺衍生物相互作用方便地制备。
• 10.1021/acs.orglett.4c02340
  作者：Yao, Jiaxin、Xiao, Yuxuan、Li, Haiyan、Yang, Xun、Du, Jiahui、Yin, Ying、Feng, Lin、Duan, Wengui、Yu, Lin

  DOI：10.1021/acs.orglett.4c02340

  日期：——

  can be arylated at the α-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C–H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.

  首次报道了通过脱硝偶联将杂芳烃与硝基芳烃进行 α-芳基化的通用方法。各种杂芳烃，包括呋喃、苯并呋喃、吡咯、吲哚、噻吩和苯并噻吩的衍生物，可以在α位以中等至良好的产率芳基化。机理研究表明，该反应通过 CMD 途径进行，其中 C-H 键激活作为速率决定步骤。此外，药物分子合成的可扩展性和适用性例证了该协议的实用性。
• US3974144A
  申请人：——

  公开号：US3974144A

  公开（公告）日：1976-08-10
• Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates
  作者：G Baziard-Mouysset、GW Tchani、JL Stigliani、M Payard、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(93)90084-r

  日期：1993.1

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.