5-methoxy-2-(4-methoxyphenyl)-3-methyl-2,3-dihydronaphtho[1,2-b]furan | 139016-16-3

• 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)-3-methyl-2,3-dihydronaphtho[1,2-b]furan
• 英文别名: (2S,3S)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-2,3-dihydrobenzo[g][1]benzofuran
• CAS: 139016-16-3
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: PSQNAPUGGLVYFO-RBZFPXEDSA-N

物化性质

• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基-1-萘酚 、 茴香烯 在 ammonium peroxydisulfate 作用下， 以 硝基甲烷 为溶剂， 反应 12.0h， 以98%的产率得到5-methoxy-2-(4-methoxyphenyl)-3-methyl-2,3-dihydronaphtho[1,2-b]furan
  参考文献：
  名称：

  共价三嗪骨架纳米粒子通过尺寸可控的限制合成增强可见光光氧化还原催化。

  摘要：

  对于无金属有机共轭聚合物基光催化剂，合成确定的纳米结构仍然具有很大的挑战性。在这里，我们报告了通过尺寸可控的限制聚合策略形成共价三嗪骨架 (CTF) 纳米粒子。与不规则的块状材料相比，均匀的 CTF 纳米粒子在二苯并呋喃的光催化形成中表现出显着增强的活性。通过将少量苯并噻二唑共聚到共轭分子网络中，可以轻松调节纳米级 CTF 的光电特性。这种电子特性的优化导致观察到的光催化效率进一步提高，与块状材料相比，总共提高了 18 倍。

  DOI：

  10.1002/anie.202007358

文献信息

• Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols
  作者：Travis R. Blum、Ye Zhu、Sarah A. Nordeen、Tehshik P. Yoon

  DOI：10.1002/anie.201406393

  日期：2014.10.6

  We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible‐light‐activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled, benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis

  我们报告了苯酚和烯烃的氧化[3+2]环加成反应方案，适用于一大类二氢苯并呋喃天然产物的模块化合成。可见光激活的过渡金属光催化使得过硫酸铵成为一种易于处理的良性末端氧化剂。很容易被光氧化还原催化氧化的有机底物范围广泛，表明该策略可能适用于各种有用的氧化转化。
• A Tailored COF for Visible-Light Photosynthesis of 2,3-Dihydrobenzofurans
  作者：Prakash T. Parvatkar、Sharath Kandambeth、Aslam C. Shaikh、Issatay Nadinov、Jun Yin、Vinayak S. Kale、George Healing、Abdul-Hamid Emwas、Osama Shekhah、Husam N. Alshareef、Omar F. Mohammed、Mohamed Eddaoudi

  DOI：10.1021/jacs.2c10471

  日期：2023.3.8

  Heterogeneous photocatalysis is considered as an ecofriendly and sustainable approach for addressing energy and environmental persisting issues. Recently, heterogeneous photocatalysts based on covalent organic frameworks (COFs) have gained considerable attention due to their remarkable performance and recyclability in photocatalytic organic transformations, offering a prospective alternative to homogeneous

  多相光催化被认为是解决能源和环境持续问题的一种生态友好和可持续的方法。最近，基于共价有机骨架（COFs）的多相光催化剂因其在光催化有机转化中的卓越性能和可回收性而受到广泛关注，为基于贵金属/有机染料的均相光催化剂提供了一种有前途的替代方案。在此，我们报告了Hex-Aza-COF-3作为一种无金属、可见光激活和可重复使用的多相光催化剂，用于合成 2,3-二氢苯并呋喃，作为一种药学相关的结构基序，通过酚类与烯烃的选择性氧化 [3+2] 环加成反应。此外，我们证明了通过 [3+2] 环加成反应合成天然产物 (±)-conocarpan 和 (±)-紫檀素是使用Hex-Aza-COF-3作为多相光催化剂的重要步骤。有趣的是，吩嗪和六氮杂苯并菲作为刚性杂环单元存在于Hex-Aza-COF-3中加强共价键，增强可见光区的吸收，并缩小能带，导致光催化反应中优异的活性、电荷传输、稳定性和可回收性，这从超快
• Reactivity of naphthol towards nucleophiles in anodic oxidation
  作者：Hesham R El-Seedi、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4020(02)00829-3

  日期：2002.9

  Reactivity of the anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles has been investigated. The reaction with electron-rich alkenic nucleophiles such as 1-methoxy-4-propenylbenzene 2 and isosafrole 3 gave a very high yield, whereas the reaction with dihydropyran 4 and dihydrofuran 5 gave a moderate yield, but with ethyl vinyl ether 6 gave a very low yield of the substituted dihydronaphthofuran derivatives 7-10 and 12, respectively. Unexpectedly, the glycosyl derivative 11 was preferentially produced rather than naphthofuran 10 upon using 5 as a nucleophile. In addition, the dimers 15 and 16 were obtained in moderate yield without addition of nucleophile to 1. The mechanism of the oxidation reactions including the [3+2] and [5+2] cycloaddition were discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Anodic oxidation of 4-methoxy-1-naphthol
  作者：Hesham R. El-Seedi、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4039(02)00544-0

  日期：2002.4

  Anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles provided the corresponding products 8 - 12 and the dimers 13 and 17 were also produced. The reaction mechanism of the oxidation reaction including the [3 + 2] cycloaddition was investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.