2-benzyl-6-methylbenzofuran

• 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-benzyl-6-methylbenzofuran
• 英文别名: 2-Benzyl-6-methyl-1-benzofuran；2-benzyl-6-methyl-1-benzofuran
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: ZBKABAGXRHTSRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-(1-hydroxy-3-phenylprop-2-yn-1-yl)-5-methylphenol 在 异氰酸叔丁酯 、 palladium diacetate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到2-benzyl-6-methylbenzofuran
  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

• Palladium-catalyzed intermolecular coupling of 2-haloallylic acetates with simple phenols, and sequential formation of benzofuran derivatives through the intramolecular cyclization
  作者：Takumi Udagawa、Yukiko Tsuchi、Ikuma Takehara、Masaki Kogawa、Hirotaka Watanabe、Mitsuaki Yamamoto、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1016/j.tet.2017.10.001

  日期：2017.11

  synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 2-haloallylic acetates with simple phenols in the presence of a base. The reaction proceeded through the intermolecular attack of the nucleophile on the central carbon atom of the π-allyl group, carbon-halogen bond cleavage, and sequential intramolecular cyclization.

  我们在碱的存在下，通过2-卤代烯丙基乙酸盐与简单酚的钯催化反应，完成了2-取代的苯并呋喃衍生物的合成。该反应通过亲核体对π-烯丙基的中心碳原子的分子间攻击，碳-卤素键的裂解以及依次的分子内环化而进行。
• Synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed intermolecular coupling of 2-fluoroallylic acetates with phenols
  作者：Takumi Udagawa、Masaki Kogawa、Yukiko Tsuchi、Hirotaka Watanabe、Mitsuaki Yamamoto、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2016.12.011

  日期：2017.1

  We investigated the intermolecular coupling reaction of 2-fluoroallylic acetates with simple phenols by the [Pd(C3H5)Cl]2, DPPF, and KHMDS at 100 °C for 16 h, and succeeded in obtaining 2-substituted benzofuran derivatives in good to high yield through the C–F bond activation and intermolecular cyclization.

  我们研究了[Pd（C 3 H 5）Cl] 2，DPPF和KHMDS在100°C下16 h的2-氟烯丙基乙酸酯与简单酚的分子间偶联反应，并成功获得了2-取代的苯并呋喃衍生物。通过CF键活化和分子间环化，具有良好至高产的效果。
• Palladium-catalyzed intermolecular coupling of 3-substituted propargylic carbonates with phenols: Synthesis of 2-substituted benzofuran derivatives
  作者：Hirotaka Watanabe、Masataka Okubo、Kouichi Watanabe、Takumi Udagawa、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2017.06.023

  日期：2017.7

  accomplished the synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 3-substituted propargylic carbonates with phenols. The 2-substituted benzofuran derivatives were obtained through the intermolecular coupling of the 3-substituted propargylic carbonates with phenols, and sequential intramolecular cyclization reaction.

  我们通过3-取代的炔丙基碳酸酯与酚的钯催化反应完成了2-取代的苯并呋喃衍生物的合成。通过3-取代的炔丙基碳酸酯与苯酚的分子间偶联和随后的分子内环化反应获得2-取代的苯并呋喃衍生物。
• 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.