5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran | 139016-12-9

• 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-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran
• 英文别名: corsifuran A；2,3-dihydro-5-methoxy-2-(4-methoxyphenyl)benzofuran；5-Methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran
• CAS: 139016-12-9
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: KEACUMVIRAXAES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran 在 亚碘酰苯 、 C₇₂H₅₂MnN₂O₂⁽¹⁺⁾*F₆P^(1-) 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(S)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran
  参考文献：
  名称：

  环状苯甲醚的氧化动力学拆分

  摘要：

  据报道，锰通过不对称的C（sp 3）-H氧化反应催化了环苄醚的氧化动力学拆分。实际的方法适用于范围广泛的1,3-二氢异苯并呋喃，其在α位置带有多种官能团和取代基，并具有非常有效的对映歧化作用。该策略的普遍性通过另一种五元环状苄基醚，2,3-二氢苯并呋喃和六元6H-苯并[c]苯二酚的有效氧化动力学拆分得到了进一步证明。进一步探索了否则难以获得的生物活性分子的直接后期氧化动力学拆分。

  DOI：

  10.1002/anie.202009594
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 iron(III) chloride 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 碘 、 1-羟基苯并三唑 、 caesium carbonate 、 magnesium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 68.0h， 生成 5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran
  参考文献：
  名称：

  铁和铜催化的芳基C–N和C–O键的形成合成功能化的吲哚和二氢苯并呋喃

  摘要：

  描述了一种简单有效的一锅两步分子内芳基C–N和C–O键形成过程，该过程可利用铁和铜催化制备各种苯并稠合的杂环骨架。对活化的芳基环进行高度区域选择性，三氟甲磺酸铁（III）催化的碘化，然后进行铜（I）催化的分子内N-或O-芳基化步骤，生成二氢吲哚，二氢苯并呋喃和六元类似物。该方法的一般适用性和官能团耐受性由新木脂素天然产物（+）-奥布他呋喃的全合成例示。还进行了使用Fukui函数的DFT计算，从而为高度区域选择性的芳烃碘化过程提供了分子轨道原理。

  DOI：

  10.1021/acs.joc.8b02888

文献信息

• Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent
  作者：Didier Bérard、Marc-André Giroux、Léanne Racicot、Cyrille Sabot、Sylvain Canesi

  DOI：10.1016/j.tet.2008.05.114

  日期：2008.8

  Treatment of various substituted phenols in the presence of iodobenzene diacetate, perfluorinated alcohols and furan, allylsilanes or cyclic enol ethers promotes an oxidative annulation process in moderate to useful yields. In only one step, this method produces different heterocyclic rings such as dihydrofuranobenzofurans, tetrahydrofuranobenzofurans, tetrahydropyranofurans, and dihydrobenzofurans

  在碘代苯二乙酸酯，全氟化醇和呋喃，烯丙基硅烷或环状烯醇醚的存在下处理各种取代的苯酚可促进氧化环化过程，产率中等至有用。在仅一步中，该方法产生不同的杂环，例如二氢呋喃苯并呋喃，四氢呋喃苯并呋喃，四氢吡喃呋喃和二氢苯并呋喃。
• Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C−O Bond Formation under Mild Conditions
  作者：Joseph Alvarado、Jeremy Fournier、Armen Zakarian

  DOI：10.1002/anie.201605648

  日期：2016.9.12

  A method for the synthesis of dihydrobenzofurans by a direct aryl C−O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates.

  描述了一种通过直接形成芳基 CO 键来合成二氢苯并呋喃的方法。该反应的机械途径与之前描述的类似转化不同，允许温和的反应条件，预计与功能化底物兼容。
• Synthesis, Characterization, and Reaction of a Both Inter- and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene-Trifluoroacetic Acid Complexes
  作者：Masaharu Yudasaka、Toshifumi Maruyama、Eiji Yamaguchi、Norihiro Tada、Akichika Itoh

  DOI：10.1002/ejoc.201701521

  日期：2018.1.31

  An ortho‐substituted ether‐oxygen‐coordinated pseudocyclic iodosylbenzene–trifluoroacetic acid (pcISB‐TFA) complex was synthesized and characterized by X‐ray crystallographic analysis. TFA suppresses the disproportionation by both coordination of the oxygen atom to the iodine(III) center through secondary bonding and by hydrogen bonding to the oxygen anion.

  的邻-取代的醚氧的协调pseudocyclic亚碘酰苯，三氟乙酸（pcISB-TFA）络合物的合成和表征通过X射线晶体学分析。TFA通过氧原子通过二次键与碘（III）中心的配位以及氢与氧阴离子的键合来抑制歧化。
• Phenol and Aniline Oxidative Coupling with Alkenes by Using Hypervalent Iodine Dimer for the Rapid Access to Dihydrobenzofurans and Indolines
  作者：Yasuyuki Kita、Toshifumi Dohi、Tomofumi Nakae、Yosuke Toyoda、Daichi Koseki、Hiroko Kubo、Tohru Kamitanaka

  DOI：10.3987/com-14-s(k)14

  日期：——

  A highly reactive hypervalent iodine dimer, [Ph(CF3COO)I]-O-[I(OCOCF3)Ph], is utilized as successful promoter in the oxidative phenolic coupling with styrenes leading to 2-aryldihydrobenzofurans. The extensions of the substrates in this study have led to the development of a new expeditious construction of the pyrroloindoline structure from aniline and enamide derivatives.
• Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives
  作者：Bradley D. Gates、Peter Dalidowicz、Andrew Tebben、Shaopeng Wang、John S. Swenton

  DOI：10.1021/jo00033a040

  日期：1992.3

  Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative. The yield of product in this electrochemical oxidation depends upon the ratio of phenol to styrene derivative, current density, and to a lesser extent the amount of supporting electrolyte. While p-methoxyphenol and 4-methoxy-3-methylphenol give good yields of the dihydrobenzofurans using 1:1 molar ratio of reactants, 3,4-dimethoxyphenol requires a 3-4 molar excess of the styrene derivative for a comparable yield of product. Although 4-methoxy-1-naphthol shows yields comparable to p-methoxyphenol in the anodic cycloaddition reaction, 1- and 2-naphthol gave very low yields of product. Qualitatively, trans- and cis-1,2-dimethoxy-4-propenylbenzene show similar yields in the cycloaddition reaction. Many of these same substrates were examined using iodobenzene bis(trifluoroacetate) as oxidant, and the same products were formed as in the electrochemical oxidations noted above. However, for the reaction of 2-naphthol and 1,2-dimethoxy-4-propenylbenzene the iodobenzene bis(trifluoroacetate) oxidation gave a much better yield of the product. A mechanism involving reaction of a phenoxy radical-styrene radical cation pair is considered and discussed.