2-phenyl-4-methoxybenzofuran | 24534-42-7

• 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: 2-phenyl-4-methoxybenzofuran
• 英文别名: 4-methoxy-2-phenylbenzofuran；4-methoxy-2-phenyl-benzofuran；4-Methoxy-2-phenyl-1-benzofuran
• CAS: 24534-42-7
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: QYBANIMGAVLZHC-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  362.8±22.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-methoxybenzofuran 在 碘 、 氢化铝 作用下， 以 乙腈 为溶剂， 以83.2%的产率得到2-phenylbenzofuran-4-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

  摘要：

  Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to multiple targets to ensure clinical effectiveness and reduce toxicity. We synthesised a series of 2-arylbenzofuran derivatives and evaluated their in vitro activities. 2-Arylbenzofuran compounds have good dual cholinesterase inhibitory activity and β-secretase inhibitory activity. The IC50 value of compound 20 against acetylcholinesterase inhibition (0.086 ± 0.01 µmol·L-1) is similar to donepezil (0.085 ± 0.01 µmol·L-1) and is better than baicalein (0.404 ± 0.04 µmol·L-1). And most of the compounds have good BACE1 inhibitory activity, of which 3 compounds (8, 19 and 20) show better activity than baicalein (0.087 ± 0.03 µmol·L-1). According to experimental results, 2-arylbenzofuran compounds provide an idea for drug design to develop prevention and treatment for AD.

  DOI：

  10.1080/14756366.2021.1940993
• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 在 sodium acetate 、 乙酸酐 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-phenyl-4-methoxybenzofuran
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

  摘要：

  Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to multiple targets to ensure clinical effectiveness and reduce toxicity. We synthesised a series of 2-arylbenzofuran derivatives and evaluated their in vitro activities. 2-Arylbenzofuran compounds have good dual cholinesterase inhibitory activity and β-secretase inhibitory activity. The IC50 value of compound 20 against acetylcholinesterase inhibition (0.086 ± 0.01 µmol·L-1) is similar to donepezil (0.085 ± 0.01 µmol·L-1) and is better than baicalein (0.404 ± 0.04 µmol·L-1). And most of the compounds have good BACE1 inhibitory activity, of which 3 compounds (8, 19 and 20) show better activity than baicalein (0.087 ± 0.03 µmol·L-1). According to experimental results, 2-arylbenzofuran compounds provide an idea for drug design to develop prevention and treatment for AD.

  DOI：

  10.1080/14756366.2021.1940993

文献信息

• AuCl₃-Catalyzed Synthesis of Highly Substituted Furans from 2-(1-Alkynyl)-2-alken-1-ones
  作者：Tuanli Yao、Xiaoxia Zhang、Richard C. Larock

  DOI：10.1021/ja0466964

  日期：2004.9.1

  Highly substituted furans have been synthesized by the reaction of 2-(1-alkynyl)-2-alken-1-ones and various nucleophiles under very mild reaction conditions in good to excellent yields. Gold and some other transition metals are efficient catalysts for this reaction.

  高度取代的呋喃已通过 2-(1-炔基)-2-链烯-1-酮和各种亲核试剂在非常温和的反应条件下以良好至极好的产率反应合成。金和其他一些过渡金属是该反应的有效催化剂。
• Synthesis of Highly Substituted Furans by the Electrophile-Induced Coupling of 2-(1-Alkynyl)-2-alken-1-ones and Nucleophiles
  作者：Tuanli Yao、Xiaoxia Zhang、Richard C. Larock

  DOI：10.1021/jo0510585

  日期：2005.9.1

  induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions. Various nucleophiles, including functionally substituted alcohols, H2O, carboxylic acids, 1,3-diketones, and electron-rich arenes, and a range of cyclic and acyclic 2-(1-alkynyl)-2-alken-1-ones readily participate in these cyclizations. Iodine, NIS, and PhSeCl have proven

  由AuCl 3催化或由亲电试剂诱导的2-（1-炔基）-2-链烯-1-酮与亲核试剂的偶联在非常温和的反应条件下可提供高取代率的呋喃，收率好至极佳。各种亲核试剂，包括功能性取代的醇，H 2 O，羧酸，1,3-二酮和富电子芳烃，以及各种环状和非环状的2-（1-炔基）-2-烯烃-1-酮参与这些环化。碘，NIS和PhSeCl已证明在此过程中作为亲电子试剂是成功的。使用已知的有机钯化学方法，可以很容易地将所得的含碘呋喃加工成更复杂的产品。
• Efficient Synthesis of Benzofurans Utilizing [3,3]-Sigmatropic Rearrangement Triggered byN-Trifluoroacetylation of Oxime Ethers: Short Synthesis of Natural 2-Arylbenzofurans
  作者：Norihiko Takeda、Okiko Miyata、Takeaki Naito

  DOI：10.1002/ejoc.200601001

  日期：2007.3

  synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic oracyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP

  开发了一种制备苯并呋喃的新合成方法。该方法的关键步骤是由肟醚的酰化引发的 N-三氟乙炔-羟胺的 [3,3]-σ 重排。TFAA 已被证明是诱导 [3,3]-sigmatropic 重排合成环甲环二氢苯并呋喃的最佳试剂。另一方面，发现 TFAT-DMAP 系统对于构建各种苯并呋喃是最有效的。该反应的合成效用通过没有羟基保护的天然苯并呋喃的短合成来证明。Stemofuran A 的合成是通过酮与芳氧基胺的缩合以及随后与 TFAT-DMAP 在四步合成中的反应来完成的，总产率为 72%。相似地，Eupomatenoid 6 和 Coumestan 通过肟醚与 TFAT-DMAP 的反应合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A facile synthesis of benzo(b)furan derivatives including naturally occurring neolignans via regioselective lithiation of ortho-cresols using the bis(dimethylamino)phosphoryl group as a directing group.
  作者：Mitsuaki WATANABE、Mutsuhiro DATE、Kenji KAWANISHI、Takako HORI、Sunao FURUKAWA

  DOI：10.1248/cpb.39.41

  日期：——

  A facile synthesis of 2-arylbenzo[b]furans via directed lithiation of ortho-tolyl tetramethylphosphorodiamidates as the key step is described. Lithiation of ortho-tolyl tetramethylphosphorodiamidates at -105°C followed by reaction with aromatic esters and then acidic treatment led to 2-arylbenzo[b]furans in modest overall yields. The utility of this strategy has been demonstrated in regioselective and short syntheses of the naturally occurring neolignans carinatin, eupomatenoid-1, and eupomatenoid-13.

  本研究介绍了一种通过原甲苯基四甲基磷二酰胺酸盐的定向石炭化反应作为关键步骤，轻松合成 2-芳基苯并[b]呋喃的方法。在 -105°C 下对原甲苯基四甲基磷二酰胺进行石蜡化反应，然后与芳香族酯类发生反应，再进行酸处理，最终以适度的总收率制备出 2-芳基苯并[b]呋喃。在天然新木质素 carinatin、eupomatenoid-1 和 eupomatenoid-13 的区域选择性和短期合成中，证明了这种策略的实用性。
• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.