2-benzyl-7-methoxybenzofuran

• 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-7-methoxybenzofuran
• 英文别名: 2-Benzyl-7-methoxy-1-benzofuran
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: SLNNXGOFCOXCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (7-methoxybenzofuran-2-yl)(phenyl)methanone 在 三甲基氯硅烷 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以81%的产率得到2-benzyl-7-methoxybenzofuran
  参考文献：
  名称：

  NaBH 3 CN-TMSCl对酰基苯并[b]呋喃，芳香族醛和酮的还原性，选择性脱氧

  摘要：

  芳香醛，酮和酰基苯并[b]呋喃已用氰基硼氢化钠和温和的亲电子试剂三甲基氯硅烷进行了还原脱氧。

  DOI：

  10.1016/s0040-4039(98)01519-6

文献信息

• DERIVATIVES OF BENZOFURAN OR BENZODIOXOLE
  申请人：——

  公开号：US20020128290A1

  公开（公告）日：2002-09-12

  An oxygen-containing heterocyclic compound represented by following Formula (I): 1 wherein R 1 and R 2 independently represent hydrogen, lower alkyl, cyano, —(CH 2 ) n —E 1 —CO—G 1 (wherein E 1 represents a bond, O, or NH; and G 1 represents hydrogen, substituted or unsubstituted lower alkyl, OR 6 , or NR 7 R 8 ; and n represents an integer of 0 to 4), or the like; R 1 and R 2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R 2 , and R 11 or R 13 described below are combined to form a single bond; R 3 represents hydrogen, phenyl, or halogen; R 4 represents hydroxy, lower alkoxy, or the like; A represents —C(R 9 )(R 10 )— or O; B represents O, NR 11 , —C(R 12 )(R 13 )—, or —C(R 14 )(R 15 )—C(R 16 )(R 17 )—; D represents (i) —C(R 18 )(R 19 )—X— (wherein X represents —C(R 21 )(R 22 )—, S, or NR 23 ), (ii) —C(R 19a )═Y— [Y represents —C(R 24 )—Z— (wherein Z represents CONH, CONHCH 2 , or a bond), or N], or (iii) a bond; and R 5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  以下是由下式（I）表示的含氧杂环化合物： 其中R1和R2独立地表示氢、较低的烷基、氰基、—（CH2）n—E1—CO—G1（其中E1表示键、O或NH；G1表示氢、取代或未取代的较低烷基、OR6或NR7R8；n表示0到4的整数），或类似物；R1和R2结合表示与相邻碳原子一起形成饱和碳环；或R2，以及下文描述的R11或R13结合形成单键；R3表示氢、苯基或卤素；R4表示羟基、较低的烷氧基或类似物；A表示—C（R9）（R10）—或O；B表示O、NR11、—C（R12）（R13）—或—C（R14）（R15）—C（R16）（R17）—；D表示（i）—C（R18）（R19）—X—（其中X表示—C（R21）（R22）—、S或NR23）、（ii）—C（R19a）═Y—［Y表示—C（R24）—Z—（其中Z表示CONH、CONHCH2或键），或N］，或（iii）键；R5表示芳基、芳香杂环基、环烷基、吡啶-N-氧化物、氰基或较低烷氧羰基；或其药学上可接受的盐。
• Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles
  作者：Antonio Arcadi、Giancarlo Fabrizi、Andrea Fochetti、Francesca Ghirga、Antonella Goggiamani、Antonia Iazzetti、Federico Marrone、Giulia Mazzoccanti、Andrea Serraiocco

  DOI：10.1039/d0ra09601f

  日期：——

  palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient

  研究了钯催化的苯并呋喃-2-基甲基乙酸酯与 N、S、O 和 C 软亲核试剂的类苄基亲核取代反应。反应的成功很大程度上取决于催化体系的选择：对于氮基亲核试剂，反应与 Pd2(dba)3/dppf 反应良好，而对于硫、氧和碳亲核试剂 [Pd(η3-C3H5)Cl] 2/XPhos 效率更高。区域化学结果表明，亲核取代仅发生在 η3-(苯并呋喃基)甲基配合物的苄位上。高至优异的产率和实验程序的简单性使该方案成为制备 2-取代苯并[b]呋喃的通用合成工具。
• 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。