2-(3-chlorobenzyl)benzofuran | 1423608-39-2

• 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: 2-(3-chlorobenzyl)benzofuran
• 英文别名: 2-[(3-Chlorophenyl)methyl]-1-benzofuran；2-[(3-chlorophenyl)methyl]-1-benzofuran
• CAS: 1423608-39-2
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: PCTMDCDIIHRENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  2
• 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：
  1

反应信息

• 作为产物：
  描述：

  在 异氰酸叔丁酯 、 palladium diacetate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以69%的产率得到2-(3-chlorobenzyl)benzofuran
  参考文献：
  名称：

  Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization

  摘要：

  An unusual Pd-catalyzed isocyanide assisted 5exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.

  DOI：

  10.1021/acs.joc.5b02204

文献信息

• Impregnated Copper(II) Oxide on Magnetite as Catalyst for the Synthesis of Benzo[<i>b</i> ]furans from 2-Hydroxyarylcarbonyl Derivatives and Alkynes
  作者：Juana M. Pérez、Diego J. Ramón

  DOI：10.1002/ejoc.201600671

  日期：2016.9

  o-hydroxybenzaldehydes with alkynes in the presence of 4-methylbenzenesulfonohydrazide was carried out in ethanol as a nontoxic biorenewable solvent and in the presence of impregnated copper(II) oxide on magnetite as a heterogeneous catalyst. The catalyst can be easily removed from the reaction medium by a simple magnetic decantation, and the reaction can be performed with a very low copper loading. The in situ

  邻羟基苯甲醛与炔烃在 4-甲基苯磺酰肼存在下的偶联-烯丙基化-环化反应序列在乙醇中进行，乙醇作为无毒的生物可再生溶剂，并在磁铁矿上浸渍的氧化铜（II）作为多相催化剂存在。通过简单的磁倾析可以很容易地从反应介质中去除催化剂，并且反应可以在非常低的铜负载下进行。起始的氧化铜 (II) 纳米粒子原位还原成铜 (0) 片材使得催化剂的可回收性变得不可能。该反应的多功能性通过使用不同的邻羟基苯乙酮得到 2,3-二取代的苯并 [b] 呋喃来证明。该反应可以在克规模上进行而没有任何并发​​症。
• Benzofuran and indole synthesis via Cu(<scp>i</scp>)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene
  作者：Tiebo Xiao、Xichang Dong、Lei Zhou

  DOI：10.1039/c2ob26867a

  日期：——

  A general and practical method to synthesize 2-substituted benzofurans and indoles is described. This method employs easily accessible N-tosylhydrazones and o-hydroxy or o-amino phenylacetylenes as substrates. The reaction proceeds through a CuBr-catalyzed coupling–allenylation–cyclization sequence under ligand-free conditions.

  描述了合成2-取代的苯并呋喃和吲哚的一般和实用的方法。该方法采用容易获得的N-甲苯磺酰hydr和邻羟基或邻氨基苯基乙炔作为底物。反应在无配体条件下通过CuBr催化的偶联-烯基化-环化序列进行。
• Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization
  作者：Manda Rajesh、Nuligonda Thirupathi、Thota Jagadeshwar Reddy、Sanjeev Kanojiya、Maddi Sridhar Reddy

  DOI：10.1021/acs.joc.5b02204

  日期：2015.12.18

  An unusual Pd-catalyzed isocyanide assisted 5exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.